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D&D 5E When should I Multiclass?

Things to think about:

  • Almost every class has a big power spike at 5th level; 3rd-level spells for casters, Extra Attack for martial types. If you start multiclassing before level 5, you risk falling way behind your single-classed companions till you hit 5th in something. Consider how you can stack class abilities to compensate. As Kerleth points out, Hex + Flurry is a good monklock combo to let you make up the damage you lose by not getting Extra Attack right away.
  • If possible, it's good to stack your class levels in increments of 4 so you don't miss out on feats/ability boosts. Those are a big deal. However, it won't kill you to wait an extra level or two before getting your levels sorted into nice 4-blocks.
  • We recently got a ruling that warlock invocations use warlock level for prereqs, not character level. This killed a lot of XXX/lock builds.
  • Consider carefully what you want out of your character. I played a cleric 4/wizard 8 for a while; he was perfectly effective in his role, but in the end he was unsatisfying compared to a 12th-level single-classed wizard. I found that I wanted access to the high-level wizard spells and advanced class abilities more than I wanted access to a smattering of clerical magic and armor. If there are particular monk abilities you really look forward to, consider going for them first and multiclassing later.
Just curious, what's your motivation for dipping warlock instead of going straight monk?
 

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Few thoughts off my head

Way of Shadow Monk... is blinded by his own DARKNESS spells
Warlock Invocation Devil's Sight removes that disability and makes it a permanent advantage on rolls.
Add in the Pact of Familiar, and you can have a mobile patch of Darkness if you cast the spell on your familiar and it flies and has blindsight, a bat seems somewhat apt here.
And then we consider WOTS monk ability to shadow hop with mobile darkness, just too many possibilities, RP and in battle.

Hex allows for nice damage stacking per attack dice rolled, and Eldritch blast in case things get dicey and I want some range.
Lastly, I believe the Monk's Unarmored Defense counts as wearing no Armor?
So with the Invocation Mage Armor, that should be AC 13+DEX+WIS, crazy high AC imho.
So yeah, only 3 levels of Warlock dip for this :p
 


There are so many exceptions to the good advice others have mentioned. Go 4 levels for the feat. But, hey, go 5 levels in a martial class for the second attack. But, wait, if you are a fighter go 6 levels as they get their second feat early.

Some classes get their archetypes at level 1 (like Cleric) so maybe only go one level in that, for example. Maybe you want to be a Fighter and take one level of Cleric for... whatever... cantrips, let's say. And you get a ton of benefit for one level. Be a Knowledge Cleric and take Guidance cantrip. All of a sudden you have two more skills at Expertise level and you can cast Guidance for 1d4 extra on all your other skills, something a straight Fighter is poor at.
 

I think you should MC when there's a good story reason, when the training rules allow for it, and when you don't f*ck up intra party balance by doing so.
 


The idea of armor basically setting a Base AC that Dex adds to (such that Barbarian really has a reset base of 10+Con and Monk has a reset base of 10+Wis) instead of a simple plus is a simple and cool one, but it does take a bit of getting used to. I think that in six months' time, we'll have sorted these things out in our heads and the simplified 3e-meets-4e-at-AD&D's-house math of 5e will be second nature to us!

That said, it really seems that there is no clear single answer to "when should I multiclass?" I love that folks can give the "do it when the story calls for it" response straightly, since the system allows for that to work really just as well (you might be a level or two better or worse on paper than other options, but you have what you need when you take it). As with many questions that used to be exact-level, it seems to go to 'tiers' of levels (where you can choose to switch between classes after x, y, or z number of classes than switch back later).

The bigger question in multiclassing that I see is less When but How Many Levels, since things like ASIs/Extra Attacks/Spell Levels are affected by the ratio. That's of course a guesswork on when one thinks the campaign (or at least character) will last until. As a guy who dislikes high-level play myself (mostly in terms of the concept of how I see the characters in the world at that point, although I also prefer the power & threat level of low-mid-tiers), I tend to think of how I'd build a character to Level 10 – anything beyond that is gravy to the meat.

Of course, between backgrounds, some of the feats, and various proficiencies, one can actually do a lot of "multiclassing" in 5e without ever leaving their class (not to mention the variation within subclasses)... ;)
 

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