What are y’all’s thoughts on making a warrior of Shadow monk then multiclassing 1 level into rogue to get weapon mastery and sneak attack. Mastering a short sword and scimitar would let you use the nick to attack with both, then the darkness from the shadow monk would make both sneak attacks as well. Add to this all the unarmed strikes of the monk and you could do some pretty good damage at level 4.
If your first class is one that gets Extra Attack, you probably want to wait until you have that before multiclassing at all. But, with that in mind, multiclassing into Rogue isn't a terrible idea.
Keep in mind a couple things about how Sneak Attack works, though. It can only be used once per turn, so in your example the Shadow Monk's Darkness wouldn't make both attacks eligible for Sneak Attack. One or the other, but not both. Also, how much extra damage Sneak Attack does is purely driven by your Rogue level, so if you want it to remain useful at higher levels, you need to keep taking Rogue levels, potentially missing out on some fun Monk stuff.
If you end up taking at least three Rogue levels, Assassin is probably the most mechanically advantageous subclass to take in this situation.
Generally speaking a Monk/Rogue split is pretty limited unless you're starting in tier 3 where you can have a fully assembled build out of the gate. Both classes rely a lot on something that scales with class level- Ki/Discipline for the Monk and Sneak Attack for the Rogue- so trying to middle of the road something largely just results in a Monk who only can do a few Ki things per rest before falling back on a weak for their character level Sneak Attack. If you really really want the Nick weapon gimmick, then dipping for one level of Rogue is a little better than taking the Weapon Master feat since you get some Expertise too, but I wouldn't recommend going further for a while, especially in a running campaign you started in tier 1.
I have two big rules of thumb for multiclassing mid-campaign- always get to at least 5th level before you start splitting since there's a big jump in character performance there, and never assume you're getting more than one level beyond your current before things fizzle out, unless this is a group you've consistently done long campaigns with. Designing your character based on performance you might get at level 9 when you're still level 3 is a good way to spend a lot of time with a clunky jumble of features and have the campaign/group end before they can come together.
Really, if you're mostly interested in the Weapon Mastery, might go Fighter instead; having Two Weapon Fighting for your Light Attack will give at least as much damage as 1d6 of Sneak Attack will average and you can look at taking one more level later for Action Surge so you can do Darkness and a full set of attacks in the same turn or just stack some extra punches.
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What are y’all’s thoughts on making a warrior of Shadow monk then multiclassing 1 level into rogue to get weapon mastery and sneak attack. Mastering a short sword and scimitar would let you use the nick to attack with both, then the darkness from the shadow monk would make both sneak attacks as well. Add to this all the unarmed strikes of the monk and you could do some pretty good damage at level 4.
If your first class is one that gets Extra Attack, you probably want to wait until you have that before multiclassing at all. But, with that in mind, multiclassing into Rogue isn't a terrible idea.
Keep in mind a couple things about how Sneak Attack works, though. It can only be used once per turn, so in your example the Shadow Monk's Darkness wouldn't make both attacks eligible for Sneak Attack. One or the other, but not both. Also, how much extra damage Sneak Attack does is purely driven by your Rogue level, so if you want it to remain useful at higher levels, you need to keep taking Rogue levels, potentially missing out on some fun Monk stuff.
If you end up taking at least three Rogue levels, Assassin is probably the most mechanically advantageous subclass to take in this situation.
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Generally speaking a Monk/Rogue split is pretty limited unless you're starting in tier 3 where you can have a fully assembled build out of the gate. Both classes rely a lot on something that scales with class level- Ki/Discipline for the Monk and Sneak Attack for the Rogue- so trying to middle of the road something largely just results in a Monk who only can do a few Ki things per rest before falling back on a weak for their character level Sneak Attack. If you really really want the Nick weapon gimmick, then dipping for one level of Rogue is a little better than taking the Weapon Master feat since you get some Expertise too, but I wouldn't recommend going further for a while, especially in a running campaign you started in tier 1.
I have two big rules of thumb for multiclassing mid-campaign- always get to at least 5th level before you start splitting since there's a big jump in character performance there, and never assume you're getting more than one level beyond your current before things fizzle out, unless this is a group you've consistently done long campaigns with. Designing your character based on performance you might get at level 9 when you're still level 3 is a good way to spend a lot of time with a clunky jumble of features and have the campaign/group end before they can come together.
Really, if you're mostly interested in the Weapon Mastery, might go Fighter instead; having Two Weapon Fighting for your Light Attack will give at least as much damage as 1d6 of Sneak Attack will average and you can look at taking one more level later for Action Surge so you can do Darkness and a full set of attacks in the same turn or just stack some extra punches.