Yes, Shady, choosing is very hard in this case.
WARNING: Lots of rules rambling ahead. Read only if you are a big ol’ D&D nerd.
So last night Shady hit 6th level after a fun session fighting against the most cheerful demonic bounty hunter ever. So now I have to actually choose, Rogue or Bard? Neither option is great immediately—6th level rogue gets her expertise in Investigation and Persuasion, but nothing else changes. 1st level bard gets her a new skill, a new proficiency, a small handful of spells, and three uses of bardic inspiration per long rest.
So neither choice is about what happens at level 6; they’re really about what happens at levels 7, 8, and 9.
If Shady sticks with rogue, at 7th she’ll get evasion and more sneak attack, at 8th she’ll hit 20 Dex, and at 9th she’ll get that awesome Panache ability and still more sneak attack. If she jumps over to bard, at 7th she’ll get Jack of All Trades (double-bumping her Initiative on top of her swashbuckler boost), at 8th she’ll get Blade Flourish (which is a game-changer ability) and Two-Weapon Fighting*, and at 9th she’ll finally catch up with that 20 Dex.
The problem is, I want all of this stuff for Shady! Panache especially is something that suits her perfectly, that whole “piss off the baddie so they chase only you—but also can’t actually GET to you” annoyance/avoidance tanking strategy goes all the way back to her fight with Kresthianze the black dragon. Having a mechanical backup for what she’s been doing purely through RP would be very nice.
On the other hand, in play, Shady’s biggest weak spot is totally her AC. The pattern with her, from the mimic that one-punched her at 2nd level, to the fight in the warehouse, to fighting Gornstard the Wailer last night, has over and over been:
1) Combat starts
2) Shady gets almost one-punched before she even gets a turn
3) She spends the rest of the fight either out or reeling from the first hit
To a certain extent, this is the rules working as intended. Rogues are glass cannons, and even swashbucklers—who are intended to get in melee and stay there—are expected to jump in and out, hide, and generally be evasive more than durable. Fortunately, Uncanny Dodge is a big mitigator here—when I remember to actually USE it—but the fact remains that Shady’s paltry 16 AC is her big ol’ Achilles Heel.
But short of magic items (and man, she is looking for that Cloak Piratey Longcoat of Protection), the only ways for her to boost her AC are 1) maxing Dex, or 2) Blade Flourish—either of which she can get at 8th level, it’s just a matter of which.
20 Dex will set her AC to 17 whenever she gets attacked, before she gets a turn or after, all the time. Blade Flourish, using the Defense option, potentially adds +1d6 to her AC (typically putting it around 19), but only after she’s made an attack, and only up to three times per long rest. It also boosts her already-crazy speed and bumps her damage on the initial attack roll.
The biggest thing is that going the bard route gives Shady the 20 Dex at 9th level—which means that in terms of AC, she gets both of the boosts by going the bard route, at the expense of a bit of sneak attack, evasion (which has not been a factor so far since we don’t have a lot of fireballs flying around, but might become one if more dragons start showing up), and, of course, panache.
I dunno; I keep going around and around and not being able to land. All of this is solved by 15th level, in which she has all the bard and all the rogue she wants and everything after that is gravy… but what are the chances of any campaign getting there? Generally not considered good. That’s what makes this a tough choice—whichever direction she chooses is likely to be the only choice she gets.
-TG
*Theoretically it would also open breastplate + shield, but even if the breastplate looked like a leather battle corset, the Dex cap would make it a net wash, and I just cannot see Shady carrying a shield. Dusk does, because he’s a fighter-flavored-with-rogue, but Shady is not a gird-her-loins type.