Thoughts on Rogue (assassin 3) / Monk 2

[RealMarkP]

New campaign is starting at level 5 and will go to level ~10. I'm looking to play a ninja-like character. Of the many multiclass options for a Monk, what are the thoughts on taking 3 levels of Rogue first and 2 levels of Kense Monk?

+ Getting then jump on creatures guarantees criticals using Assassinate.
+ Use martial weapons.
+ Sneak attack.

Once I hit 3rd monk level, the Kensai's Shot would stack with sneak attack for even more damage.

Thoughts?

[Keravath]

The question is why not go monk 5 first for stuns, more ki, an ASI, extra attack? For a ninja type you might want a shadow monk which probably means going to level 6 for shadow teleport and strikes treated as magical. Then consider adding some levels of rogue perhaps? Using sneak attack means you will need to use monk weapons with the finesse property so that you can use all your abilities. I think this comes down to daggers and shortswords.

If you are a kensei then you can choose a ranged weapon as your Kensei weapon. However, using Kensei's shot uses your bonus action so you won't be able to use the rogue trick of using your bonus action to hide to obtain advantage and enable sneak attack. You will also need to wait until level 8 to get extra attack.

Finally, rogue is a great chassis but depending on how your DM runs surprise, some of the Assassin abilities may not come up very often.

[Misterwhisper]

New campaign is starting at level 5 and will go to level ~10. I'm looking to play a ninja-like character. Of the many multiclass options for a Monk, what are the thoughts on taking 3 levels of Rogue first and 2 levels of Kense Monk?

+ Getting then jump on creatures guarantees criticals using Assassinate.
+ Use martial weapons.
+ Sneak attack.

Once I hit 3rd monk level, the Kensai's Shot would stack with sneak attack for even more damage.

Thoughts?

Criticals are only auto on surprise, which is not as easy to get
As a lot op people think.

The martial weapons would still have to be ranged or finesse but longbows are the main point anyway.

Yes KS does stack with sneak attack, however you would be better off going monk 5 for extra attack or rogue 5 for more sneak attack.

I would do either not both.

Assassin is not that great after round 1.

Inquisitive is great, swashbuckler is if built right, arcane trickster is amazing and thief is great depending on what you want to do.

[CNagy]

Personally, I'd flip the levels. Kensei Monk 3/Rogue 2. The Kensei benefits are more immediately useful.

[DrowPiratRobrts]

I played something similar before Kensei came out. Might I second the recommendation for Shadow Monk (though ultimately either would be fine)?

I would go Monk 5 at the start then level to 6 then take 4 levels in Rogue.

Swashbuckler won't give you the up front burst potential of Assassin, but it's what I ended up playing with my Shadow Monk, and the increased mobility fits really well with the Monk's speed and extra attacks.

Edit: There's also a good argument for starting Rogue 3/Monk 2 and then finishing out Monk before picking up that last level of Rogue. But it really depends on the subclasses you go with and what is most important to you.

[Reevh]

I feel like Kensei wouldn't offer all that much at those levels. Shadow seems alright, though you only get the teleport at level 6. The spells you can cast are fairly cool and pretty thematic.

But if I were choosing I think I'd go for Open Hand. The ability to knock a target Prone and then follow up with attacks at advantage is priceless, especially if you have other melee characters to take advantage of it. It's somewhat reduced in benefit if you're in a party with lots of ranged attackers.

It's also pretty fun to push enemies into environmental hazards with your attacks, if available, or walls if not.

[Misterwhisper]

I feel like Kensei wouldn't offer all that much at those levels. Shadow seems alright, though you only get the teleport at level 6. The spells you can cast are fairly cool and pretty thematic.

But if I were choosing I think I'd go for Open Hand. The ability to knock a target Prone and then follow up with attacks at advantage is priceless, especially if you have other melee characters to take advantage of it. It's somewhat reduced in benefit if you're in a party with lots of ranged attackers.

It's also pretty fun to push enemies into environmental hazards with your attacks, if available, or walls if not.

Knocking them prone is only on an unarmed flurry attack, which is after the attack action so you would only be getting adv on one attack and it can’t be a sneak attack weapon because it has to be unarmed.

Open hand is great on solo monk.

[DrowPiratRobrts]

Also check with your DM to see if he or she will allow your unarmed strikes to proc sneak attacks. I've seen it ruled both ways. RAW it doesn't work, but it's well within the theme of the character and doesn't affect you that much since you can still only get sneak attack once per turn. It just gives you a little more synergy between the classes. Never hurts to ask.