Trying to feel around the inter webs for some help with a build idea I’ve been brewing for an upcoming campaign. Our campaigns usually aren’t anything to scoff at (our first went on for 2 years, and the current one for 3 years) so long term fun is highly preferred and we usually start at level 1 and end somewhere in the mid/early teens. We roll for stats but if we roll bad we are always allowed to get one stat to 18 after racial traits. So I can rely on my DEX being 18 at level 1.

The idea I can’t seem to shake is that of a magic-less Human Whip & Dagger using Smuggler/Thief. Someone who is very observant of their surroundings, and crafty in combat. 

With whips I felt going mostly rogue will offset the low damage die but sprinkling in fighter (specifically a 3 level dip to Battlemaster) will give it flexibility, off turn sneak attacks, and more shenanigans in general to keep things interesting in combat. my initial thought is Fighter 1 —> Rogue 1 —> Fighter 3 —> Rogue X but can’t decide on a rogue subclass (thief, swashbuckler, inquisitive or assassin). I feel giving up the extra skill is worth it for the more balanced saving throws and direct access to the Whip from level 1 even though heavy armor and shields won’t really come in play with the build. Any thoughts on a different level breakdown?

Also, besides having difficulty on picking a rogue subclass, I’m having a hard time choosing maneuvers post Tasha’s. Quick-toss, Riposte, and Brace all seem amazing for off turn sneak attacks. Quick-Toss is reliable but hogs BA and Reaction, Brace is reliable but inhibits the ability to use Uncanny Dodge because you Brace before getting attacked, but Riposte feels the least reliable to proc albeit gives a nice drop down menu of reactions. Besides those 3 Trip Attack, Disarming Attack (situational as heck and when it comes up most likely the receiver will have good STR), and Pushing Attack all feel very rogue-like. Any input on maneuvers would be dope!

As far as level 1 variant human feats go, stacking martial adept with superior technique fighting style feels real nice (6 superiority dice of which 4 are d8s and 2 are d6) but idk if it’s overkill. Sentinel feels nice too adding to the drop down menu of Uncanny Dodge, Riposte, Sentinel OA of standing next to another martial character. Observant feels nice thematically too as being able to read lips and have crazy high passive perception would be very helpful for a smuggler/thief. So many options… any other ideas for level 1 feats?

Any advice would be greatly appreciated folks!

Swashbucklers need to be within 5 feet of their target to swashbuckle, which is incongruous with using a whip.  The other subclasses you listed have even bigger problems with using a whip.  If I had to pick a Rogue subclass to wield a whip, I'd go with either an Arcane Trickster or a Phantom. 

Why not go straight Rogue and pick a race (elf, dwarf, etc.) that has racial weapon proficiencies you can change to a whip?  

If you want to stick with a vhuman, Observant seems to best fit your character description.  Alert might be an alternative, and more Rogue-like, variation on your idea.  Always on the lookout, even if you don’t remember everything you notice.

I also don’t see a problem with Inquisitive, as quindraco suggested above.  You can use a whip for Sneak Attack, and hence Insightful Fighting, since a whip is finesse.  If you go this route, you’ll need to get a decent WIS, probably as your second or third stat.

That’s not a bad idea. Won’t have to give up SA dice that way either. A Pallid Elf could be really strong.

Yeah Inquisitive feels the most reliable way to proc sneak attack even if the other features probably won’t come up as much.

Quote from Sisyphus_Rocks >>

Why not go straight Rogue and pick a race (elf, dwarf, etc.) that has racial weapon proficiencies you can change to a whip?  

If you want to stick with a vhuman, Observant seems to best fit your character description.  Alert might be an alternative, and more Rogue-like, variation on your idea.  Always on the lookout, even if you don’t remember everything you notice.

 That’s not a bad idea. Won’t have to give up SA dice that way either. A Pallid Elf could be really strong.

Just to pile on the full rogue train, proficiency in DEX saving throws makes Evasion that much better. It really feels great to (consistently) take 0 damage from a fireball dropped right on your head.

What you really want for off-turn SA is a teammate who takes Battlemaster. Commander's Strike is no joke.

Quote from ArntItheBest >>

You could also make this a Monk and take the Whip as your dedicated weapon (flavor it as a Rope Dart if you really want). That means that your damage will scale up with it as your monk level increases. You can even make it a Kensei Monk if you really want to lean into the weapons, and you can use Kensei's Shot with a Dagger.

Just know that in order to dual wield with a Whip and a Dagger, you will need the Dual Wielder Feat as the Whip is not light.

Oh shit I just thought you couldn’t dial wield two non-light weapons. Well ain’t that unfortunate.

Quote from scatterbraind >>

Just to pile on the full rogue train, proficiency in DEX saving throws makes Evasion that much better. It really feels great to (consistently) take 0 damage from a fireball dropped right on your head.

What you really want for off-turn SA is a teammate who takes Battlemaster. Commander's Strike is no joke.

 True, evasion and dex proficiency is pretty awesome. I didn’t think about that interaction with the level 7 evasion feature. Well rounded saves are nice, but that dex save proficiency really adds up in value when you hit 7 rogue.

Quote from pidgns >>

Quote from ArntItheBest >>

You could also make this a Monk and take the Whip as your dedicated weapon (flavor it as a Rope Dart if you really want). That means that your damage will scale up with it as your monk level increases. You can even make it a Kensei Monk if you really want to lean into the weapons, and you can use Kensei's Shot with a Dagger.

Just know that in order to dual wield with a Whip and a Dagger, you will need the Dual Wielder Feat as the Whip is not light.

Oh shit I just thought you couldn’t dial wield two non-light weapons. Well ain’t that unfortunate.

 A whip and a short sword are both 3 pounds. Yet one is light, and one isn't. And the one that isn't CANNOT be used two handed!

Absurd.

I think you'll find Swashbuckler is probably ideal for your build. 

Swashbuckler gives you better maneuverability, SA on demand and a bump to initiative which leans into your observant and ever-prepared character concept.  You'll probably find it's a little kinder to the bonus action economy as you don't need to use it on Cunning Action all the time.  If you want to use maneuvers regularly, this is a good thing.  Battlemaster as you know is a good dip, particularly for a non-magical Rogue.

Maneuvers really are wonderful on a Rogue.  A Rogue has to keep a close eye on initiative, the battlefield and positioning and maneuvers gives you more options to take advantage of openings.  I will say that Quick-Toss is a great option because you'll be in and out of combat and this gives you a touch extra range as well as extra SA.  Also as far as I know, it doesn't require a reaction, just the bonus action.  This might make it more tempting a pick.  Brace is also good if you are clever about it.  It does use your reaction but with Swash maneuverability, you have an easier time picking off enemies or going for isolated targets, while keeping yourself out of the line of fire.  Riposte and Sentinel are also great picks, as you know.

I suggest taking Rogue first regardless of how you do the level split because you'll need the skills more than the armor and weapon proficiencies from Fighter.  Rogue saves are also better for dealing with aoe.  One option is going Rogue 3 and then Battlemaster 3, before continuing with Rogue and perhaps taking another 2 levels in Fighter at some point.  That will give you the character style you want from Rogue levels and then you move quickly to the maneuvers, which helps replace a higher SA dice.  You'll also have Action Surge, which can be fun.  If you want you could also go Rogue 1/Battlemaster3-5/RogueX, which will be more in line with other martials, particularly if you go Extra Attack, but it slows SA.  It will also feel more like a Figher in play until you get more Rogue levels. 

If you go Variant Human, you can have the best of both options as you've noted, by taking Martial Adept.  There is another consideration, regarding your race and that is your weapon.  Potentially could could swap a proficiency but that might require a different race, which means sacrificing the feat.  When you'll go Fighter relatively soon, it seems a waste.  I'll also mention that while you have said you want to go with a whip, first consider how that will potentially limit you on the battlefield.  For example, the Sentinel reaction attack is limited to:  "creature within 5 feet of you makes an attack against a target other than you".  If you go Swash, there is a distance requirement but with Fancy Footwork, it's not much of an issue, but something to keep in mind.

Now, the obvious feat for most standard builds, would probably be one of the Initiate feats to grab Booming Blade, if you didn't choose Elf/Half-Elf.  Eventually, you could pair this with Warcaster to impressive effect under the right circumstances.  Note that how useful this is varies depending on the table.  The sword cantrip would certainly help in the earlier levels too.  I'm not sure you'd want this, though, as you've specified a non-magical Rogue, and often it is better to not use cantrips due to SA accuracy issues.  Sentinel is a good option as mentioned but it is very positioning dependent.  Slasher, if you do go whip, would add some crowd control and a +1 to your DEX.  Dual Wielder is another feat worth having if you want to use dual weapons, particularly as whip isn't light, but if you skip whip, some tables hand wave the drawing of weapons if you have Two Weapon Fighting Style, so judge accordingly.

Honestly, this build is lots of fun.  I don't think you'll have too many problems, no matter how you build it.

Quote from TheManyNamed >>

I think you'll find Swashbuckler is probably ideal for your build. 

Swashbuckler gives you better maneuverability, SA on demand and a bump to initiative which leans into your observant and ever-prepared character concept.  You'll probably find it's a little kinder to the bonus action economy as you don't need to use it on Cunning Action all the time.  If you want to use maneuvers regularly, this is a good thing.  Battlemaster as you know is a good dip, particularly for a non-magical Rogue.

Maneuvers really are wonderful on a Rogue.  A Rogue has to keep a close eye on initiative, the battlefield and positioning and maneuvers gives you more options to take advantage of openings.  I will say that Quick-Toss is a great option because you'll be in and out of combat and this gives you a touch extra range as well as extra SA.  Also as far as I know, it doesn't require a reaction, just the bonus action.  This might make it more tempting a pick.  Brace is also good if you are clever about it.  It does use your reaction but with Swash maneuverability, you have an easier time picking off enemies or going for isolated targets, while keeping yourself out of the line of fire.  Riposte and Sentinel are also great picks, as you know.

I suggest taking Rogue first regardless of how you do the level split because you'll need the skills more than the armor and weapon proficiencies from Fighter.  Rogue saves are also better for dealing with aoe.  One option is going Rogue 3 and then Battlemaster 3, before continuing with Rogue and perhaps taking another 2 levels in Fighter at some point.  That will give you the character style you want from Rogue levels and then you move quickly to the maneuvers, which helps replace a higher SA dice.  You'll also have Action Surge, which can be fun.  If you want you could also go Rogue 1/Battlemaster3-5/RogueX, which will be more in line with other martials, particularly if you go Extra Attack, but it slows SA.  It will also feel more like a Figher in play until you get more Rogue levels. 

If you go Variant Human, you can have the best of both options as you've noted, by taking Martial Adept.  There is another consideration, regarding your race and that is your weapon.  Potentially could could swap a proficiency but that might require a different race, which means sacrificing the feat.  When you'll go Fighter relatively soon, it seems a waste.  I'll also mention that while you have said you want to go with a whip, first consider how that will potentially limit you on the battlefield.  For example, the Sentinel reaction attack is limited to:  "creature within 5 feet of you makes an attack against a target other than you".  If you go Swash, there is a distance requirement but with Fancy Footwork, it's not much of an issue, but something to keep in mind.

Now, the obvious feat for most standard builds, would probably be one of the Initiate feats to grab Booming Blade, if you didn't choose Elf/Half-Elf.  Eventually, you could pair this with Warcaster to impressive effect under the right circumstances.  Note that how useful this is varies depending on the table.  The sword cantrip would certainly help in the earlier levels too.  I'm not sure you'd want this, though, as you've specified a non-magical Rogue, and often it is better to not use cantrips due to SA accuracy issues.  Sentinel is a good option as mentioned but it is very positioning dependent.  Slasher, if you do go whip, would add some crowd control and a +1 to your DEX.  Dual Wielder is another feat worth having if you want to use dual weapons, particularly as whip isn't light, but if you skip whip, some tables hand wave the drawing of weapons if you have Two Weapon Fighting Style, so judge accordingly.

Honestly, this build is lots of fun.  I don't think you'll have too many problems, no matter how you build it.

 Thanks for the detailed reply! This is a fantastic write up with tons of good points.

The more I’ve heard about and worked on the build it seems hard to ‘mess up’. There are so many options that while not everyone is optimal, they all have flavor and usability.

I’ve definitely narrowed down the level split I think from all the conversations I’ve had around the build to be Rogue 1 —> Fighter 1 —> Rogue 3 (or 5) —> Fighter 3 — Rogue 7. That pushes me plenty along into the level 11 range which is at our groups level up pace well over a year of gameplay. And who knows RP reasons might pull them off the set path but this gets the character to Manuevers, Evasion, and 4d6 sneak attack which is a fantastic spot to be.

Yeah the more I’ve thought about the Whip the more it feels limiting rather than freeing on a non magical rogue. The whip feels like a better fit for an Arcane Trickster rogue or a mainly fighter build. A short sword flavored as a Short Spear and a dagger feel just as thematic for the style of character I envision and allows that sweet sweet “drop down menu” style of reactions you can get on rogue with Riposte and Sentinel. Attack me an hit, Uncanny Dodge, attack me and miss Riposte, attack any melee friend near me Opp Attack. 

With whip seemingly off the table, I feel like level 1 feats become a little more free too. Rogue level 1 and Observant at level 1 for backstory building and bringing the theme together, superior technique (riposte) at fighter 1 (character level 2) to give them an option for off turn sneak attacks once a short rest, sentinel at first ASI to give me more sneak attack options, then Battlemaster for 4 more superiority dice feels like it meshes mechanics, pacing, and theme pretty succinctly.

Seems like our next campaign is going to lean into some darker dungeon style rules (as we all want to try out some more survival based gameplay) too so I’ve been considering what that means as well with interactions but most of the important resources this build requires are short rest based. And being a skillmonkey seems valuable in a campaign with more survival elements. That pillar has me leaning into the thief subclass just for the versatility it provides. Swashbuckler is mechanically stronger in combat but thief opens up the creative avenues that I love to you with in combat as I’m not the best number cruncher.

Yeah the whip is just generally not great in 5e. It feels like it's only included as a weapon bad guys wield. Really needs some support to make it work. At the very least, I don't think it breaks anything to give it the light property.

Quote from scatterbraind >>

Yeah the whip is just generally not great in 5e. It feels like it's only included as a weapon bad guys wield. Really needs some support to make it work. At the very least, I don't think it breaks anything to give it the light property.

I'm not really sure it's the whip's fault. 

I think it's this edition's inconsistencies when dealing with weapons.  First we have only a few weapons being given feat support to make them more powerful.  It's even worse when you realize they already have innate advantages in their weapon properties, (polearms and bows), that makes them already strong choices.  Support for other weapon types?  Sure, according to damage type which the aforementioned weapons can *also* benefit from. 

Then we have inconsistencies with weapon reach all through feats and class abilities (5ft to rule them all).  This can particularly be seen in the recent nerf to the blade cantrips, which means they don't work with Spellsniper, anymore.  This might have been intended to avoid use with polearms but ironically it hurts whips and thus Rogues, who are one of the few classes that can use them effectively, more. 

If things were standardized a bit better, so it read something like 'within your weapon's reach' or something similar, it would be so much easier.

Quote from pidgns >>

Seems like our next campaign is going to lean into some darker dungeon style rules (as we all want to try out some more survival based gameplay) too so I’ve been considering what that means as well with interactions but most of the important resources this build requires are short rest based. And being a skillmonkey seems valuable in a campaign with more survival elements. That pillar has me leaning into the thief subclass just for the versatility it provides. Swashbuckler is mechanically stronger in combat but thief opens up the creative avenues that I love to you with in combat as I’m not the best number cruncher.

Thief is good but not much more than most other Rogue subclasses.  It *can* shine with hi-jinks and item support but it's highly dependent on table and DM buy-in.  That said, things like oil, alchemist's fire, poison or caltrops quickly lose effectiveness unless new leveled homebrew versions are introduced.  I'll also add that there just aren't all that many options for Fast Hands in combat that make it that much better than what base Rogue can do, or what martial value other subclasses can add.  Also don't forget it uses a bonus action, which eats into your maneuver economy.  As for Second Story Work?  It doesn't come up all that much.  Even further along, the abilities are very situational.

Of course, there's no easily quantifying the fun value.  Take what you think you'll enjoy most.

Quote from scatterbraind >>

Yeah the whip is just generally not great in 5e. It feels like it's only included as a weapon bad guys wield. Really needs some support to make it work. At the very least, I don't think it breaks anything to give it the light property.

 Yeah, I'm playing an Oath of Vengeance Paladin, and I was playing with a whip and short sword before I realized that whip wasn't light. I'm going to talk to my DM about it.

I enjoyed cracking the whip and then swinging with the short sword. Lots of fun. I doubt it was an optimal build, but it was fun.

I use whip on a warcaster'd up cleric. The extra reach while still wielding a shield is just phenomenal. This feels like one of the only builds where it shines. Nearly every other character concept you'd think it thematically could work either doesn't have proficiency for it or you're trying to squeeze an extra Duel Wielder feat into for no real gain. It is really sad the weapon got treated this way. The fact it ain't light feels criminal.