D&D 5E Yeah, another 5e Monk multiclass question. Sorry in advance.

[AchwardSilence]

So I posted this the other day here and on a few other forums. Thanks to those who responded for their advice. I didn't want to resurrect that thread so I'm starting a new one with a similar but more specific question for the same character.

I think I'll take him to L11 as a reflavored Long Death Monk. After that, I'm not sure where to go up to the campaign starting level of 15. For context, keep in mind that the character is a street fighter/back alley brawler. I'm less opposed to magic as I originally was, but the more I can refluff it to feel less arcane, the better. He also should ideally be able to hold his own acceptably well in a L15-20 campaign, but he's more accustomed to 1-on-1 fights.

Here's my best options as I see them:
-Pure Monk up to 15. Benefits: 4 more Ki, 5 more feet of movement, Diamond Soul. I don't really care about the L13&15 features, and though Diamond Soul is awesome I don't know if it would be as good for the flavor of this character as three levels in another class.
-Barbarian Bear Totem 3. Benefits: Best HP of all the options, Advantage on Dex saving throws, damage bonus and advantage if I ever find myself using Str, and crazy damage resistance. Also, since I'm building to 15 from scratch, I could technically take Barb first if I wanted its Unarmored Defense instead of the Monk's.
-Rogue Swashbuckler 3. Benefits: Expertise, 2d6 sneak attack with a finesse weapon, cunning action, increased initiative, free semi-disengage, is a ing swashbuckler.
-Ranger (especially if the DM allows UA Revised) Hunter or Deep Stalker 3. Benefits: Fighting Style, advantage on some attacks, bonus damage against some enemies, Hunter's Mark, [Hunter] situational extra 1d8 damage per turn, [Stalker] situational extra speed and attack, nice in low-light to dark conditions, extra spell.
-Fighter Battle Master 3. Benefits: Fighting style, 3-13 HP healing per short rest, action surge, better maneuver options than by simply taking the Martial Adept feat. Oooh, and artisan's tools.

For the final level, I'd get an ASI/Feat regardless of class as long as I keep it to the two, but I don't know if extra Ki or a better hit die would be better.

I'm building this more for fun than optimization, and honestly the pure Monk feels the least fun, followed probably by the Ranger.

I'm sorry for the long post, but I'm still new to 5e, and haven't figured out its quirks yet. Thanks for your time, and any advice is greatly appreciated.

 

[mellored]

I'd say battlemaster. You get a number of tricks to add to your ki aand action surge.

 

[UngeheuerLich]

Monk to level 14 of course. Diamond soul is one of the best features of any class. It makes you more or less immune to magic. Level 15 is as dead as possible. The phb ranger level 1 comes close.
So I would make it level 14 monk after a single level of barbarian. I would make STR one of my higher attributes. CON the highest and Dexterity in between.
So Barbarian1/Monk14
Too bad your friend is the half orc and you the half elf. From an optimizer perspektive the opposite would have been better.
So
Str 13
Dex 15+1 +2
Con 15+1 +2 +2
Int 8
Wis 12
Cha 8+2

 

[AchwardSilence]

I'd say battlemaster. You get a number of tricks to add to your ki aand action surge.

I'm currently leaning toward that or a Hunter Ranger for the extra damage, but Bearbarian's damage resistance is very tempting.

 

[AchwardSilence]

Too bad your friend is the half orc and you the half elf. From an optimizer perspektive the opposite would have been better.

Yeah, but that was what we were going for by playing against type. The eloquent, highly-skilled, charismatic half-orc and the hit first, hit second, ask questions later maybe but only while hitting again, half-elf.

 

[doctorbadwolf]

Rogue: expertise helps round a character out. A monk with a rogue splash can be an unstoppable free runner, climber, etc, if that is relevant to your campaign. The swashbuckler bits make you impossible to pin down. Also dex/con/wis is, IMO, just a better stat lineup for any character that doesn't need high str for class stuff. Even with barb, you can't ignore dex, and rogue gets you skills, swashbuckler goodies, SA, cunning action, and theives cant, which seems rather appropriate for the character.

Ranger: don't discount the cool factor of a pet monkey. seriously, though, ranger gets you fighting style (I recommend mariner for this character, as much for the climb speed as for anything else), favored enemy, bat explorer, which no longer specifies wilderness, along with everything you mentioned. i only recommend this if DM allows the revised ranger.

I dont like fighters enough to comment there. I don't recommend barbarian, just because it runs counter to the rest of the concept, to me.

 

[AchwardSilence]

Ranger: don't discount the cool factor of a pet monkey.

The question now, of course, is whether I'd rather have the damage output of a Hunter, or an ape companion named Ambassador Pickles who smokes cigars, wears a bowler hat, and grapples enemies from behind while I run up and beat them down (plus he can use his reaction to shank them in the kidney when I hit)?

 

[doctorbadwolf]

The question now, of course, is whether I'd rather have the damage output of a Hunter, or an ape companion named Ambassador Pickles who smokes cigars, wears a bowler hat, and grapples enemies from behind while I run up and beat them down (plus he can use his reaction to shank them in the kidney when I hit)?

I mean, every crew needs an Ambassador. The question practically answers itself.