Yeah, another Monk MC question. Sorry in advance.

[AchwardSilence]

So I posted this a bulid-help question about making a L15 street boxer the other day here and on a few other forums (sorry I can't just link, but my post count isn't high enough yet I guess). 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.

[Aembrosia]

I vote ranger

[Specter]

I'd definitely go BM, for Goading Attack. Taunting people into punching you is where the money is at.

[Maxilian]

I would go with a BM Ranger... mostly because you could have an Ape pet and have it as your sparring partner.

The Ape will have Prof in 2 skills (grappling and Athletic or Acrobatic -whatever you see fit for the build-)

Note: You would start lvl 4 Ranger, at lvl 5 you would get the ability to attack with your pet -using your pets reaction-(That's supposed to substitude the Extra attack, but you got extra attack from Monk, so you could say this is a way to combine both)

Note2: This is more of a silly idea that would be fun with your build (this is not the most optimized character but its not going to be bad either)

[SillyPopeNachos]

I'd definitely go BM, for Goading Attack. Taunting people into punching you is where the money is at.

This feels so much like a proper street fight tactic. You can possibly also trip people and then start curb-stomping. 16 levels in monk gets great saves, and the last 4 in Battle Master gets dirty tricks.

[AchwardSilence]

This feels so much like a proper street fight tactic. You can possibly also trip people and then start curb-stomping. 16 levels in monk gets great saves, and the last 4 in Battle Master gets dirty tricks.

I like this. My problem is that I can't quite decide if he's a) the dirty fighter, b) the guy that doesn't go down when he should, or c) the guy who hits harder than you'd expect.

Battle Master or Rogue work with a). Bearbarian works with b), though a Long Death Monk is already pretty good at staying standing. Hunter, sort of Rogue, or Battle Master with the right maneuvers work for c). He's definitely more of a city boy, but a few levels of Ranger can be reasonably fluffed that way, and it's easy enough to justify that he's more worldly and traveled by higher levels anyway.

[AchwardSilence]

I can also go 14/3/3, which loses 2 ASI/feat bumps, but I can totally see this guy as an underdog with lots of situational dirty tricks. Another big question is if, by starting at Level 15, I want to start off with Diamond Soul or with the Level 3 features of a multiclass.