D&D 5E Level Plan For A Multiclassed Swashbuckler?

[Allistar1801]

So this isn't really meant to be for optimization or anything, just a fun little character build for an up and coming character of mine and I'm curious as to how people will critique it. I've already talked to the DM about how I want to RP the character and have a story arc in mind, so the character will have at least something going for him no matter if this plan goes face down.

Concept- Dashing Duelist/Jack Sparrow-ish character
Rolled Stats (racial mod included)- 10str, 19dex, 12con, 11int, 16wis, 16cha
Race- Kenku
Background- Sailor
Starting Class- Rogue
Starting Proficencies- Acrobatis, Athletics, Deception(x), Insight, Perception, Performance(x), Sleight of Hand, Stealth

Level	Class	Gained Abilities
1	Rogue	Sneak Attack (1d6), Expertise-aka(x), and Thief's Cant
2	Fighter	Weapon/Armor Proficiency, Duelist Fighting Style, and Second Wind
3	Fighter	ACTION SURGE
4	Rogue	Cunning Action
5	Rogue	Swashbuckler Archetype, and Sneak Attack (2d6)
6	Rogue	ASI (+1 dex, +1 Con/ 20 Dex, 13 Con)
7	Fighter	Samurai Archetype, Bonus Persuasion Proficiency
8	Fighter	Feat (Resilient-Con/ 14 Con+saving throw proficiency)
9	Fighter	Extra Attack
10	Fighter	Feat (Martial Adept- Disarming Attack, and Riposte)
11	Rogue	Uncanny Dodge, and Sneak Attack (3d6)
12	Rogue	Expertise (Persuasion, Perception)
13	Rogue	Evasion, and Sneak Attack (4d6)
14	Rogue	ASI (+2 Con/ 16 Con)
15	Fighter	Elegant Courtier (More Persuasion, and Wisdom Save Proficency
16	Fighter	ASI (+2 Con/ 18 Con)
17	Fighter	Indomitable
18	Fighter	Tireless Spirit
19	Fighter	Extra Attack (2)
20	Fighter	ASI (+2 Con/ 20 Con)

Ending Level Breakdown- Fighter 12, Rogue 8

Ending proficiencies- Acrobatics, Athletics, Deception(x), Insight, Perception(x), Performance(x), Persuasion(x) Sleight of Hand, Stealth

Like I said definitely not optimized, but a lot of fun to be sure. He's beefy(lots of HP, lots of good saves), he's evasive(lots of damage prevention and mobility), he's got alright damage(between sneak attack, extra attacks, action surge, and other bonuses), and he's got the skills for outside of combat (especially social encounters). Haven't really run the numbers on how much damage or average HP, but I can't imagine it being too bad. The main factor drawing me to this is the RP value and the idea of an Italian fencer full of that classic machismo sailing the high seas and charting his own course in life and becoming captain. But enough about all that, what do y'all think? Tell me why I'm wrong about every single decision I've made in this post and what I should do instead.

 

[Zardnaar]

I would probably go Rogue one/fighter 1 then take the next 3 or 7 levels in rogue.

Otherwise it looks very good already and it's just personal preference as I assume you want action surge early.
Either way personally I would only take 8 rogue levels mixing in fighter/ranger levels.

 

[Allistar1801]

I would probably go Rogue one/fighter 1 then take the next 3 or 7 levels in rogue.

Otherwise it looks very good already and it's just personal preference as I assume you want action surge early.
Either way personally I would only take 8 rogue levels mixing in fighter/ranger levels.

Ranger levels? I havent really looked into that class at all. What could be gained from multiclassing into ranger?

 

[Blue]

You have a concept and a story. You avoid pitfalls of multiclassing like missing ASIs. You are good to go.

Another thing you have going is that you have ability scores higher then point buy, which means quicker access to feats or to advancing secondary ability scores. Add that to the extra fighter one and I like how you're taking advantage of it.

If you are looking for some suggestions, read below. But you don't have to - your plan is fine.

First is what level does the DM reasonably expect the game to go up to? Most games spend the vast majority of play in the first two tiers, and many never get up to the teens.

Then, plan on coming together at latest about half that level - so your concept is "firing" for at least half your time of play. (If you are starting above 1st or the DM is explicitly leveling quickly for the first few levels, then instead aim for being fully online for the average of starting and ending level.)

5th and 11th levels are a big power bumps for straight-classed characters, and that's reflected in foes. Make sure that you aren't far behind at those levels. For example you don't have the fighter 5th level boost (extra attack) until 9th, or the rogue 5th level boost (uncanny dodge plus 3d6 SA) until 11th. You may want to do less switching back and forth until you have 5th in one class or another.

SA means you need to land one blow to do your big damage - having multiple attacks helps land it. Fighter is about multiple attacks each adding decent damage. Both of those benefit from more attacks, but you aren't set up for two weapon fighting, and extra attack is delayed until 9th. I worry that you might have a lot of "whiff" rounds, where you get one attack, miss, and that's it.

Samurai ability to for three rounds give yourself advantage will help a little, but that's about one combat a day if you use them all one after another so it's not a large help. It also scales with number of attacks (mroe attacks = more rolls at advantage), so the big gap between getting it and extra attack slows how much it helps. With other rogues besides Swashbuckler it helps get sneak attack by providing Adv if there is no ally nearby, but Swashbuckler helps alleviate that pain with an additional way to get SA.

If Samurai fits your character concept, go with it. If it was picked for nifty bonuses, others like Battlemaster might work better. Precision can make sure you land those sneak attacks, and the Superiority Dice are only used when you miss instead of before like Samurai's advantage, and they recover on a short rest instead of long. Riposte, which I see you have planned with Martial Adept, help you deliver it again since it's a different turn. With BM you will have more superiority dice then Martial Adept and they get bigger.

(Samurai is no means bad. It does help land blows, help set up SA, and gives a greater chance of crits which multiply all your SA dice.)

You mentioned being willing to look into other multiclasses. Bard (College of Swords) gives a number of swashbucklery flourishes that both fit mechanically but also may fit thematically. The problem is that it really wants bard 5 to refresh those bardic inspirations on a short rest instead of a long, would want some more CHR for more dice, and overlaps fighter in both giving extra attack.

Now, if you are playing into your teens (of level), a big concern would be wisdom saves. Raising you CON gives bonuses to HPs as well, but raising your WIS isn't that useful. You may want to move your +2 CON ASIs ones sooner, and take Resilient (WIS) instead. This way both will be getting better, instead of having the same WIS save at 1st and 20th.

 

[Zardnaar]

Ranger levels? I havent really looked into that class at all. What could be gained from multiclassing into ranger?

Hunter ranger gives you hordebreaker, a combat syle, some spells, and an extra attack at 5th. Shield proficiency as well. Player was a Mastermind rogue who didn't dual wield

 

[Mort]

Mechanically, I think it's pretty good.

I also like the concept.

But Kenku? How are you going to play the can't speak except by mimicry part? Seems a bit at odds with being a dashing swashbuckler (then again, it could make for a really interesting character).

 

[DEFCON 1]

Mechanically, I think it's pretty good.

I also like the concept.

But Kenku?

Well, he did say he wanted to play a 'Jack SPARROW' type of character...