Gift of alacrity for an extra d8

Quote from TheSytheRPG >>

My post a little bit above took all of this into affect, though that bonus you presented is simply a +48 maximum, which is still very good. Mine above, however, is a +80 maximum above, which uses some of the things you mentioned as well as a few others.

 You might consider a cursed luckstone sure it has a downside but advantage on initiative or enhance ability can give advantage(even going party wide).  Then you free up those barb levels to put in things like Chronomagic for like 2nd level spell to reroll and kick up the chances of higher end rolls or just generally customizing character how you want.  Otherwise what a fantastic list of options I just winced at that huge dip.  The spell gives up guidance but there’s a nice flair to aoe speed up plus still an impressive self boost

I managed to get this insanity on maximum rolls and an unhealthy number of magic items.

The insane setup:

PLAYER

30 Dexterity: +10
Harengon Race with Ioun Stone of Mastery: +7
Swashbuckler Rogue 3 with 30 Charisma: +10
Gloom Stalker Ranger 3 with 30 Wisdom: +10
War Mage Wizard 2 with 30 Intelligence: +10
Bard 2 Jack of All Trades: +3
Fiend Warlock 6 Dark One's Luck: +1d10
(As mentioned by TheSytheRPG, Champion Fighter 7 does not stack with Jack of All Trades, since we cannot add half our proficiency twice. It was replaced by Fiend Warlock to get a +1d10 instead of +4)
Alert Feat: +5
Sword of Kas with Guardian Benefit: +1d10+2
Scorpion Armor: +5
Stone of Good Luck: +1
Mythic Conflux Feat, with Headband of Initiative: +2 (as pointed out by TheSytheRPG)

ALLIES

Bardic Inspiration: +1d12
Guidance: +1d4
Peace Cleric Emboldening Bond: +1d4
Gift of Alacrity Spell: +1d8
Oath of the Watchers Paladin Aura of Sentinel, attuned to Ioun Stone of Mastery: +7
Wild Magic Barbarian Bolstering Magic: +1d3

This chaos gives you an absolute maximum of 142 to Initiative, and an absolute minimum of 99. If for some ungodly reason you tie someone in Initiative, you have 30 Dex and a flat +62.

A magic item with the Guardian minor property would add +2 bonus to initiative (DMG143)

Guardian. The item whispers warnings to its bearer, granting a +2 bonus to initiative if the bearer isn't incapacitated.

Barbarians already have advantage at level 7;

Feral Instinct

By 7th level, your instincts are so honed that you have advantage on initiative rolls.

Additionally, if you are surprised at the beginning of combat and aren’t incapacitated, you can act normally on your first turn, but only if you enter your rage before doing anything else on that turn.

So the cursed luckstone is unneeded as it currently stands. Though I believe there are ways to go even higher than what I have now otherwise. i shall investigate again lol

I must ask- since when did Oath of the Watcher's Paladin gain an initiative bonus? They have aura of the sentinal which aids your proficiency bonus, but that wouldn't stack with the champion fighter, nor would you even have enough levels left to grab them.

Ok next question, if I roll 100 on my initiative check, do I get an extra action every turn? Or a half hour warning about the ambush the enemy hasn't decided they want to do yet?

Quote from Wlyr >>

Ok next question, if I roll 100 on my initiative check, do I get an extra action every turn? Or a half hour warning about the ambush the enemy hasn't decided they want to do yet?

No, but your odds of going first are excellent.

Are there any monsters better at Initiative than a Will-o'-Wisp/Elder Tempest or maybe Pazuzu?  A Will-o'-Wisp's +9 means that its max Initiative is 29, so if you have +29 to Initiative, you'll automatically go before it.  With a +30, you'll beat Pazuzu without a roll.

EDIT: Autolinking Pazuzu doesn't seem to work, but he has Dex 30, so +10 to Initiative.

Quote from Wlyr >>

Ok next question, if I roll 100 on my initiative check, do I get an extra action every turn? Or a half hour warning about the ambush the enemy hasn't decided they want to do yet?

 Winning by 1 or by 99 doesn't confer additional benefits. You go first, fast and furious!

By the way, the paladin adding proficiency, the bard jack of all trades adding 1/2 proficiency and the champion fighter adding 1/2 proficiency don't stack. You can't add a proficiency bonus more than once as far as I know unless you have expertise or some other ability that explicitly allows it. The Ioun Stone of Mastery increases your proficiency bonus by +1 so this would probably be best used in combination with the paladin aura effect that adds proficiency to initiative.

I am guessing the d12 bardic inspiration and paladin aura are from allies?

Quote from David42 >>

By the way, the paladin adding proficiency, the bard jack of all trades adding 1/2 proficiency and the champion fighter adding 1/2 proficiency don't stack. You can't add a proficiency bonus more than once as far as I know unless you have expertise or some other ability that explicitly allows it. The Ioun Stone of Mastery increases your proficiency bonus by +1 so this would probably be best used in combination with the paladin aura effect that adds proficiency to initiative.

 Expertise doesn't add it more than once - it doubles it.  The RAW is that you add no more than once, multiply no more than once, and halve no more than once.

However, that's for your own proficiency bonus.  You can add an infinite number of proficiency bonuses from other people.  That means a bard, champion, or harengon gets their native initiative bonus from proficiency on top of any nearby watcher paladin.

Here we go again, from the top:

I return again, simply because I find it fun to do needless research to the point where I'm insane just to figure out funny possibilities. This time, I'm going to set out the previous maximum initiative bonus I set of +80, which resulted in an absolute maximum of 100! It seems, though, that I've recently be "bested" - if you can even call it that - so I'm going to see if I can go further than I originally thought! Maybe I'll even breach +100 this time!

Step One: The Main Character
Character Stats:
--> We are going to assume the gods favor our dice and we roll straight sixes for every single stats; all of our base stats are 18. Assuming the gods of D&D themselves are funding this escapade, we can also assume we have access to any magic item in any number. As a self set restriction, we are only including D&D Beyond official content, however we will include Critical Role content from any book due to Wildemount being officially published. Okay? Okay.

Character Race:
--> Stats are not a worry here, so we want any race that can aid us otherwise. Because a feat would benefit us the most here, we will use the Custom Lineage option from Tasha's, which allows us to take a feat of our choosing.

Classes Required:

• Level 2 Wizard (Chronurgy Magic) --> Adds intelligence (+10) to initiative rolls, Gift of Alacrity spell adds +1d8 to initiative.
• Level 4 Ranger (Gloomstalker) --> Adds wisdom (+10) to initiative rolls, provides an ASI.
• Level 4 Rogue (Swashbuckler) --> Adds charisma (+10) to initiative rolls, provides an ASI.
• Level 1 Cleric (Any Domain) --> Blessing spell adds +1d4 to initiative.
• Level 2 Bard (Any College) --> Jack of All Trades adds half proficiency bonus (+3) to initiative.
• Level 7 Barbarian (Any Primal Path) --> Feral Instinct provides advantage on initiative rolls, provides an ASI.
• As a note; while we have enough levels to include the Champion Fighter's Bonus (at the cost of replacing the barbarian's levels), which is half proficiency bonus, the ability itself states that you must not already use this bonus. Therefor, since the bard's Jack of All Trades feature already grants this bonus, it cannot be included. Sorry Lexluxray, but it doesn't work.

ASI/Feature Choices: 

• Feature: Mythic Conflux. This is an ASI from the Tal'dorei Campaign Setting, the first D&D supplement published by Critical Role. This was published before Wildemount, but as said, any D&D content from Critical Role is being included here. The benefit of this ASI is the user gains an extra attunement slot, allowing us more magic item flexibility.
• ASI #2 - Feature: Alert. Grants a +5 to initiative rolls. Simple enough.

Magic Items Required:

• 6 of each of the following magic item: Manual of Bodily Health/Gainful Exercise/Quickness of Action, Tome of Clear Thought/Leadership and Influence/Understanding. Each of these provide a permanent +2 increase to each of your current stats and their maximums, though D&D typically caps stats at an ultimate 30. Therefore, that is where we will be stopping with the benefits of these items; all of our stats, at this point, are 30, or a +10. This is important later.
• Sword of Kas. This is a magical artifact, so we gain two benefits while attuned; the first is the "Spirit of Kas" ability which grants a +1d10 bonus to initiative. Additionally, one of the minor beneficial properties - which the Sword of Kas can have due to being an artifact - is Guardian, from the DMG, which grants an additional +2 bonus to initiative as well. This is the first attunement slot we use.
• Scorpion Armor. This is an item from Tomb of Annihilation which gives us a +5 bonus to initiative; simple enough. This takes our second attunement slot.
• Headband of Initiative. Another item from Critical Role, only it is from the first season campaign itself (again, I said I'm using *anything* Critical Role. Discount this if you will). It is a simple +2 bonus to initiative, at the cost of our third attunement slot.
• Stone of Good Luck. A very simple +1 to all ability checks and saving throws, which does include initiative. This takes up our fourth attunement slot (which was, again, granted by the Mythic Conflux feature)

Extra Characters:

• Level 20 Oath of Watchers Paladin --> Grants proficiency bonus to initiative rolls of nearby party, which can be upped by using taking the Mythic Conflux feat again, granting a fourth attunement slot, and then grabbing four Ioun Stones of Mastery, each of which increase your proficiency bonus by 1, with no stipulation saying it cannot stack. This can increase the paladin's proficiency to a grand +10, which is then granted to their allies in the form of an initiative bonus.
• Level 20 (Any College) Bard --> Can grant a +1d12 of bardic inspiration which can be used to benefit initiative rolls.

Grand Total:

• Bonuses granted by stats include our dexterity, wisdom, intelligence, and charisma bonuses due to our subclass choices, and each of our stats are set to 30 due to the magic manuals and tomes, granting us a +10 for each respective category. This is a total bonus of +40 for this section.
• Bonuses granted by classes include a +3 from the bard's Jack of All Trades trait which grants half your proficiency modifier which could be +6 at level 20. Barbarian also grants us advantage on initiative rolls.
• Bonuses granted by spells include Blessing, which grants a +1d4, and Gift of Alacrity, which grants a +1d8.
• Bonuses granted by features include Alert, which grants a +5 to initiative.
• Bonuses granted by magical items include a +1d10 and a +2 from the Sword of Kas due to the Spirit of Kas ability and the Guardian minor beneficial property, a +5 from Scorpion Armor, a +2 from the Headband of Initiative, and a +1 from the Stone of Good Luck, totally to a +1d10 and a +10.
• Bonuses granted by additional characters include a +10 from a level 20 Oath of Watcher's Paladin with 4 Ioun Stones of Mastery and a +1d12 from a Level 20 Bard's Bardic Inspiration.

The Absolute Total:

1d20 (Natural Roll) + 40 (Stat Bonuses) + 3 (Jack of All Trades) + Advantage (Feral Instinct) + 1d4 (Blessing) + 1d8 (Gift of Alacrity) + 5 (Features) + 1d10 + 10 (Magic Items) + 1d12 + 10 (Additional, involved characters) or 1d20+40+3+Advantage+1d4+1d8+5+1d10+10+1d12+10 which simplifies down to 1d20+1d12+1d10+1d8+1d4+68

The minimum, assuming all dice roll a 1: 73
The average, assuming all dice roll their averages: 95
The maximum, assuming all dice roll max: 124 --> This means we did, in fact, have a maximum bonus of 104!!!

Quote from TheSytheRPG >>

 

(cut)

Harengon from Wild Beyond The Witchlight I believe provides +prof to initiative, meaning you don't need 7 levels of fighter or 2 levels of bard.

You can replace 7 Barbarian with 1 Wild Magic Sorcerer would provide advantage (Tides of Chaos) at the cost of wild magic, and 6 levels Warlock (Fiend) for +1d10. Wild Magic is a pretty big cost but it's not like your going to be playing this build anyways lol.

(Edit: speaking of wild magic, another party member level 6 wild magic sorcerer could add +1d4 to your roll)

Idk if Ioun Stones of Mastery (see oath of watchers paladin part) stack, but I can't find anything that says otherwise so cool.

(Edit: Rogue 11 would get reliable talent, but that wouldn't increase the max, just the average. Also gl trying to fit that into this build lol)

Other than that absolutely amazing job. One of the best parts of optimizing D&D, being absolutely unnecessary but absolutely stunning.

twilight domain gives advantage on initiative rolls, vigilant blessing.
you can just use it 1 year in advance or smth and also the guidance

Player: HAHA I go first with an an initiative count that I have to use an IBM supercomputer to calculate HAHAHA by the way I attack

DM: So now that your turn is over onto the next monster and, ooooh

Player's Character: *Dies from a monster that came 1 turn after him because he had no abilities to attack or any defence*

So I got this higher by removing bard and barbarian. Making race  Harengon and 10 lvls of fighter battle master. This adds full PB instead of half from bard and 1d10 superiority die. Also add a paladin friend with oath of watcher for + 6. 
With everything, our entire roll becomes 1d20 + 40 (Dexterity, Intelligence, Wisdom, Charisma) + 5 (Alert) + 5 (Scorpion Armor) + 6 (Harengon) + 2 (Sword of Kas - Minor Beneficial Property) + 2 (Headband of Initiative) + 1 (Stone of Good Luck) + 1d10 (Sword of Kas - "Spirit of Kas") + 1d8 (Gift of Alacrity) + 1d4 (Guidance) + 1d10 (battle master) + 6 (watcher paladin)  for min 71 and max 119

I'm a DM(my first time DMing after only playing D&D for about... less than a year...? Maybe four to seven months - max) with a total of six players. So, I like to mess around on D&D Beyond & create random NPCs that are probably WAY to overpowered(most of them are level 20 NPCs but eh-). So I found this thread & thought to myself "huh, my players would probably hate my guts if I created a character with way too high of an Initiative Modifier... Time to pull a sneaky,". Of course, I won't use this NPC in my ACTUAL campaign that I DM in, but I just wanted to do this for fun. So, I followed all of the amazing advice given on here, & got a +33 modifier to Initiative, a +3 thanks to Jack of Trades, I'm 60% sure I could use Bardic Inspiration, adding a d6 to the roll, I'm 40% sure that I could use Remarkable Athlete, a +5 thanks to Dread Ambusher, another +5 thanks to Rakish Audacity, a +5 thanks to Tactical Wit, another +5 thanks to Alert, I'm 10% sure I could use Favored By The Gods, which adds 2d6, an added d10 thanks to the Sword of Kas, Advantage on Initiative thanks to the Rod of Alertness, a +5 to Initiative thanks to the Scorpion Armor, & an added d4 thanks to Guidance. This NPC has a 30 in Dex, a 20 in Intelligence, Wisdom, & Charisma, which helps with the Initiative Bonus as well. Now, I, yet again, began to think to myself; "What about AC, Saving Throws, & HP?". So, what did I do? I took two Leather Armors, giving me a +2, which, adding my +10 in Dex, gives me a 12 AC by itself - then, I added the +2, making it 14, thanks to a Shield. Rod of Alertness gives me a +1 to both AC & Saving Throws if I use Protective Aura, which gives me a 15(only if I use Protective Aura). If I were to take my AC & add Scorpion Armor, that would give me an 18, & I'm roughly 30% sure that taking eight levels in Fighter, with a Champion subclass, probably did something as well. Taking four levels in Wizard, with the War Mage subclass, gives me Arcane Deflection, which, when used(it's used as a reaction), can give the character either (A) a +2 to AC, or (B) a +4 to a failed Saving Throw. I also took Shield, so, as a reaction, I could cast Shield, giving me a +5 to AC until the start of my next turn. I have no idea what else I did to make a 24 AC, but I mean, it works- Now, for HP, the Bard feature, Song of Rest, allows creatures to gain an extra 1d6 HP & Second Wind, thanks to Fighter, allows me to regain 1d10+8 HP. So I have a 91 HP, by itself, a 24 AC, & a +33 to Initiative, not including any feats & spells that I can use. 

I think I did all of the math wrong & I probably messed something up somewhere in this mess(^), so please tell me if I did -

 Edit: My bad, it's not a +33, it's a +38(without all of the feats & spells that I can use).

Re: sadomsa

Your build is lower because you forgot to include the d12 bardic inspiration from a level 20 bard ally, as well as the Bless spell (min 80, max 135)

Personally instead of 10 levels in Fighter, I prefer 1 level Wild Magic Sorcerer (Tides of Chaos grants advantage), 6 levels Fiend Warlock (+1d10). Getting battlemaster is a good idea though I didn't think about, and I did have a 3 level gap, so... 3 levels battlemaster (+1d8 through Ambush).

So my build looks like (assuming no CR HB stuff):

Race: Haregon

Class: Chronurgy Wizard 2, Gloomstalker Ranger 4, Swashbuckler Rogue 3, 1 Wild Magic Sorcerer, 6 Fiend Warlock, 3 Battlemaster Fighter, 1 Cleric (any)

Feats: Alert, Lucky, last ASI idk

Same Magic Items & Ally boosts, Throw in a level 5 wizard for fortune's favor, it doesn't increase any of our modifiers but why not?

Paladin goes down to 9 because no unoffical CR content, and wait there's no Artificer Flash of Genius on there. Let's just add in a casual +12 (6 prof then +6 ioun stones).

Then add a cleric, druid, or Paladin's cantrip fighting style doesn't matter, just get Guidance going.

So bonuses are: DEX, WIS (Gloomstalker), CHA (Swashbuckler), INT (Chronurgy), PROF (Haregon), 5 (Alert), 1d10 (Fiend), 1d8 (Ambush), 1d4 (Bless), 1d4 (Guidance), 1d8 (Gift of Alacrity), 1d10 + 2 (Sword of Kas), +1 (Stone of Good Lucky), +5 (Scorpion Armor), +9 (Oath of Watchers), +12 (Artificer), +1d12 (Bardic Inspiration)

Plus Advantage (Wild Magic Surge), and can roll two additional d20s (Lucky & Fortune's Favor)

1d20 + 10 + 10 + 10 + 10 + 6 + 5 + 1 + 5 + 9 + 12 + 1d10 + 1d8 + 1d4 + 1d4 + 1d8 + 1d10 + 1d12

min: 86, max: 154

so this is 4d20 keep highest 1 (normal + adv + fortune's favor + lucky), tossing stuff into anydice grants a mean of 16.48 which looks right I think, let's just round that to 16.5

avg 126

With all cr content including unofficial it's just +4 (+2 headband of initiative, +1 paladin, +1 artificer) btw. If you assume you can't stack Ioun Stones then uh, idk find some other magic item that increases prof there has to be a couple. If not then it's just a -7 (-2 paladin, -5 artificer). Can use a second cleric as well to remove that cleric level in exchange for a extra ASI but I just didn't know what to spend it on.

<p>function: highest NUMBER:n of DICE:d {<br /> result: {1..NUMBER}@DICE<br />}</p>
<p>output [highest 1 of 4d20]</p>

 Major credit for TheSytheRPG, I'm just taking their word on a lot of the magic item stuff. If anything is wrong feel free to reply.

edit: cleric and DevilInTheShadows3 accidently sniped me lol

I did some more research and broke it farther.

Ability Scores

1. High Elf for +2 DEX and +1 INT and long life span
2. Point Buy for a Stat array of the following 
   
   • STR   DEX   CON   INT   WIS   CHA
   •    8       16      9        14     14      14
3. Either has a copious amounts of the Ability Score manuals or 1 of each for DEX, INT, WIS, & CHA
4. Then spend the next 8 Centuries reading those books. Possibly done after leveling a bit to take that down to 7 centuries. This will get the Scores up to the increased maximum of 30(+10).

Classes (I am going to use critical role content Explorer's Guide to Wildmount and Tal'dorei Campaign Guide.)

1. First we take 7 levels in fighter with the Gunslinger subclass's 7th level feature which adds your proficiency bonus to initiative rolls and gives us two ASI. (Explorer's Guide to Wildmount)
   • Alternatively you could use the the Oath of Watchers Paladin (Tasha's Cauldron of Everything). Though this would be only one ASI and for reasons you will see later we do not want this class on this character.
2. Second we take 4 Levels in Ranger: Gloomstalker to add our Wisdom modifier to our initiative rolls and get and an ASI. (Xanathar's Guide to Everything, pg. 42)
3. Third we take 4 Levels in Rogue: Swashbuckler to add our Charisma modifier to our initiative rolls and get and an ASI. (Xanathar's Guide to Everything, pg. 47)
4. Fourth we take 4 Levels in Wizard: School of Chronurgist to add our Charisma modifier to our initiative rolls, get an ASI, and gain gift of Alacrity. (Explorer's Guide to Wildmount)
5. Fifth we take our final level in Cleric: Peace Domain to get guidance, bless, and the first level feature: Emboldening Bond which function like Bless(without Concetration) but is not the spell. (Tasha's Cauldron of Everything, pg. 33) 

We are now at a +40(Dexterity, Intelligence, Wisdom, Charisma)+6(proficiency)+1d4(Bless or Guidance)+1d4(Emboldening Bond)+1d8(Gift of Alacrity). This is a minimum of +49 or maximum of +62.

Now to deal with the 5 ASIs

1. We grab Alert for +5 to initiative. (Player's Handbook pg. 165)
2. Grab Mythic Conflux for an additional attunement slot. (Tal'dorei Campaign Guide)
3. Martial Adept Feat and we will take Ambush as one of our maneuvers to add 1d6 superiority die to initiative checks. (Player's Handbook pg. 168)
4. The other 2 could be used for whatever we desire.

We are now at a +40 (Dexterity, Intelligence, Wisdom, Charisma) +6 (quickdraw) +5 (Alert) + 1d6 (Ambush Maneuver) +1d4 (Bless or Guidance) +1d4 (Emboldening Bond) +1d8 .(Gift of Alacrity). This is a minimum of +55 or maximum of +73.

Magic Equipment and Boons. 

1. We are going to get the Sword of Kas which adds 1d10 onto initiative rolls. (Dungeon Master's Guide)
2. We are going to pick up the Sentinel Shield giving us advantage on initiative rolls. (Dungeon Master's Guide)
3. Scorpion Armor gives +5 to initiative rolls. (Tomb of annihilation)
4. Headband of Initiative give +2 to initiative rolls. (Tal'Dorei Campaign Setting)
5. Luckstone(Dungeon Master's Guide) or Ioun Stone of Mastery(Dungeon Master's Guide) will both give a +1 to initiative through our setup. We will choose the Ioun Stone of Mastery which will become relevant later.
6. Shield Guardian/Amulet to store Bless or Guidance and cast on us. Alternatively you could use a Charm/Potion of Heroism. These two I do not believe would stack since the charm says you are under the affects of a Potion of Heroism and the Potion says you are under the affects of Bless. Based upon the combining magical/game effects(PHB pg 204/DMG pg. 252) the Charm of Heroism, Potion of Heroism, and the spell Bless would not stack.
7. One of the items detailed in 1-5 has the Guardian effect(Dungeon Master's Guide pg 143) which is +2 to initiative rolls. Similarly to #6 above I believe this affect can only be applied to a character once despite technically being from different sources.
8. Boon of Luck adds 1d10 to an ability check. (DMG pg. 232)

We are now a total of 1d20 (Advantage from Sentinel Shield) + 40 (Dexterity, Intelligence, Wisdom, Charisma) + 6 (Quick Draw) + 5 (Alert) + 1d6 (Ambush Maneuver) + 5 (Scorpion Armor) + 2 (Guardian on one of the magic items) + 2 (Headband of Initiative) + 1 (Ioun Stone of Mastery) + 1d10 (Sword of Kas) + 1d10 (Boon of Luck) + 1d8 (Gift of Alacrity) + 1d4 (Guidance) + 1d4 (Bless) +1d4 (Emboldening Bond). Our current total is minimum 69 and maximum of 127.

Variant Rules.

1. Speed Factor Initiative Modifiers. (Dungeon Master's Guide, pg. 271)
   • Size Tiny gives +5 Size Small gives +2. We will either change race to Gnome for the +2 and get the immortality boon or wish too be a tiny sized Elf for the +5.
   • While attuned to the Sword of Kas, we will not be attacking with it. Instead, we are going to attack with a light or finesse weapon for +2.
2. Hero Points (Dungeon Master's Guide, pg. 264) 
   • This level of character would have 15 Hero Points that could be spent (only 1 per roll) on an ability check. These Hero Points add 1d6 to a d20 roll.
3. Proficiency Die (Dungeon Master's Guide, pg. 263)
   • Changes our proficiency from +6 to +1d12 which will increase our overall maximum
   • We have the Ioun Stone of Mastery Equipped and Attuned increasing our proficiency bonus to +7 or proficiency die +1d14

After implementing those rules and using wish to exploit one of them, our total is now: 1d20 (Advantage from Sentinel Shield) + 40 (Dexterity, Intelligence, Wisdom, Charisma) + 1d14 (Quick Draw variant rule: Proficiency Die) + 5 (Alert) + 1d6 (Ambush Maneuver) + 5 (Scorpion Armor) + 2 (Guardian on one of the magic items) + 2 (Headband of Initiative) + 1 (LuckStone/Ioun Stone of Mastery) + 1d10 (Sword of Kas) + 1d10 (Boon of Luck) + 1d8 (Gift of Alacrity) + 1d4 (Guidance) + 1d4 (Bless) +1d4 (Emboldening Bond) + 5 (Speed Factor Size:Tiny) +2 (Speed Factor using light or finesse weapon) + 1d6 (Hero Points). This new minimum is 72 with a maximum of 148.

On our own, I believe this is as far as we can go. But now we are going to bring help. Let us build a party to indulge our narcissistic need to be the best ever at initiative.

The Party

1. Paladin 7/Sorcerer 6/Druid 6
   1. Paladin: Oath of Watchers' 7th Level feature Aura of the Sentinel adds proficiency bonus (+6 or +1d12 to) initiative rolls of themselves and creatures they designate within 10 feet. (Tasha's Cauldron of Everything pg. 55)
      • This Sorcadin Druid will be given an Ioun Stone of Mastery. This will increase the proficiency bonus to +7 and presumably the proficiency die to a d14.
   2. Sorcerer: Wild Magic 6th Level feature Ben Luck adds 1d4 to an ability check. (Player's Handbook pg. 103)
   3. Druid: Circle of Stars 6th Level feature Cosmic Omen allows the addition of 1d6 to an ability check about to be made. (Tasha's Cauldron of Everything)
2. Bard 15
   1. This Bard we brought along to fuel our narcissistic need for validation and to provide a d12 Bardic Inspiration
3. Artificer 7 (Probably the reason we got this far)
   1. Give them a couple centuries to read and achieve 30(+10) Intelligence
   2. Use Flash of Genius on our grand initiative narcissist (Tasha's Cauldron of Everything, pg. 13)
4. One of the Three have the Boon of Fate adding 1d10 to our initiative roll (Dungeon Master's Guide pg. 232)

Grand Total

1d20 (Advantage from Sentinel Shield) + 40 (Dexterity, Intelligence, Wisdom, Charisma) + 1d14 (Quick Draw variant rule: Proficiency Die) + 5 (Alert) + 1d6 (Ambush Maneuver) + 5 (Scorpion Armor) + 2 (Guardian on one of the magic items) + 2 (Headband of Initiative) + 1 (LuckStone/Ioun Stone of Mastery) + 1d10 (Sword of Kas) + 1d10 (Boon of Luck) + 1d8 (Gift of Alacrity) + 1d4 (Guidance) + 1d4 (Bless) +1d4 (Emboldening Bond) + 5 (Speed Factor Size:Tiny) +2 (Speed Factor using light or finesse weapon) + 1d6 (Hero Points) + 1d14 (Aura of the Sentinel) + 1d4 (Bend Luck) + 1d6 (Cosmic Omen) + 1d12 (Bardic Inspiration) +10 (Flash of Genius) +1d10 (Boon of Fate)

Minimum: 87

Average 148.83

Maximum: 204

Sorry for ressing and old post but with 3 levels in fighter we can get the battlemaster subclass with and pick up Ambush which is another d8 to initiative!