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I'm putting together a Shadow Monk/Assassin Rogue character concept for a new game of D&D 5e but I have little experience with multi-classing. So, what should I consider when deciding which class to start as?

For example, starting as a Rogue seems to make the most sense to me - at face value you get more skill proficiencies, more equipment and generally seem more useful to a starting party.

I know my AC can take a bit of a hit due to leather armour vs. unarmoured defence but are there any other considerations I should be aware of?

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Factors to consider, in order of importance (IMHO):

  1. Weapon proficiencies: You get more weapon profs by taking Rogue first, though not much benefit to those due to Monk's Martial Arts feature.
  2. Skills: In terms of number and desirability. Rogue gets you 4 skills from a pretty decent list, whereas Monk only gets you 2, from a more limited list (and you only get 1 when MCing Rogue, so, net -1. You do get Thieves' tools, which is nice).
  3. Saving throw proficiencies: Which pair protects you best, both in number and severity of threats. Dexterity and Intelligence (Rogue) protect against fewer threats than Dex and Str (Monk). Having said that, at L14, Monks get Diamond Soul, granting proficiency in all saving throws.
  4. Misc proficiencies: Rogue gets you Thieves' tools, vs. Monks' artisan tool/musical instrument.
  5. Starting equipment: Rogues get far more lavish starting equipment, including the very desirable Rapier, Thieves' Tools, Shortbow, and Burglar's pack (given your shadowy inclination). However, you can't use your Rapier with Martial Arts.
  6. Starting HP: Not as important in the long run, but useful in the low-levels (at most, a difference of 6 HP, considering Barbarian vs. Sorc/Wiz). In this case, not relevant at all, since both classes are d8.

That's all I can think of, hope this helps!

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    \$\begingroup\$ You might want to review point 3. Consulting the spell filters at DNDBeyond, I see 12 spells that use Str as a Saving throw, but only 2 that use Int. It's possibly this changes with monster ability saving throws, but I'd still hand it to STR because of your ability to resist being shoved, grappled or otherwise moved. Not quite saving throws, but similar enough. Other than that, good breakdown. \$\endgroup\$
    – keithcurtis
    Jun 7, 2017 at 23:40
  • \$\begingroup\$ Done! Thanks for the note—I took your word for it, since I think Maze and Feeblemind are the two? \$\endgroup\$
    – Khashir
    Jun 15, 2017 at 19:04

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