I figured I'd make a quick list of all of the multiclass options I'm considering for my next playthrough, to get your honest thoughts on them, potential cheesiness aside. I've also tried to, where appropriate, include a little snippet about how each character would function, story-wise, and what faction they'd support.
1. Sage (Helwalker/No-Subclass Wizard): An arcane lancer (Or spirit lancer, if you don't mind the fact that Dragon's Dogma Online will never get a Western release) that uses Wizard defensive buffs to somewhat mitigate the extra damage taken from Helwalker. Uses Dance of Death/Enduring Dance to stack wounds, in conjunction with Wizard buffs to mitigate damage. Also uses a secondary Grimoire with Evocation spells. High Might, Perception, and Intellect. Pale Elf, from the White.
Faction: VTC for convenience
Personality: A knowledge seeker, with designs on a position as an Archmagus. This character has an almost predatory fascination with acquiring new information, often for its own sake, which is why he was willing to subject himself to the death rite in order to become a Helwalker in the first place. Has strong ties to Wael and the Hand Occult, and went with Wael's decision in the first game.
Gameplay Pros - Absurdly high Might and Intellect at max Wounds (30/30). Nice mix of defensive buffs and offensive spellcasting with two different grimoires. At max level, can use melee weapons at range. Can AoE stun using Citzal's Spirit Lance with Stunning Surge. 20% Fire Damage lash.
Gameplay Cons: High susceptibility to damage. Average to low Con means I can only take a few hits. Not as many Afflictions as the Spellblade, and a lot of attacks target Fortitude.
Roleplay Pros: Heavily invested in the Circle of Archmagi plot in the main game, and in the third DLC. More likely to go out of my way to find quests, and has more leeway in resolving situations. Also, not blood-loyal to the VTC, so more justification for doing other Factions' quests.
Roleplay Cons: Less opportunities to involve myself with the Circle in the main game, save for the one quest chain. That said, plenty of opportunities for offscreen storytelling.
2. Spellblade (Streetfighter/Wizard): Another variant on the arcane lancer, with Rogue skills to spread afflictions in an AoE. Low Might, but (Absurdly) high Con to allow for a large health pool/staying bloodied longer to make use of Streetfighter's damage boosts. Human, from Rauatai.
Personality: A pro-Rauatai intelligence agent whose primary interest in the Deadfire is furthering the RDC's interests in the region. While the knowledge hunter allies with the VTC out of convenience/for the funding opportunities offered, the Spymaster is fiercely loyal to his motherland.
Gameplay Pros: Streetfighter can outspeed Monk with the right armor because of their insane attack speed buff when Flanked or Bloodied. Also has access to additional Sneak Attack damage, and can spread afflictions and DoTs to lots of enemies.
Gameplay Cons: Has to be Flanked and/or Bloodied for the best result, so it's a much riskier playstyle. High Constitution comes at the cost of low Perception, and also doesn't result in 'much' more HP than the Sage, because of Spellblade's lower base health pool.
Roleplay Pros: The RDC provides plenty of opportunities for quests through bounties and such, and there's certainly nothing preventing you from taking unaffiliated bounties as well.
Roleplay Cons: Not a lot of ways to create a "Pro-Rauatai" save in the first game, so there's a bit of a disconnect there. Plus, you're essentially 'locked in' to supporting the RDC if you choose to RP this to the hilt, meaning you logically shouldn't take other Faction quests (Or complete them in the most destructive ways possible) and it locks you out of a good portion of bounties (Which might have something you want, gear-wise).
Right now, I'm leaning more toward the Sage, simply for a bit more of a freewheeling adventuresome playstyle that focuses a lot more on the Wizardly aspects of the Wizard multiclass. I will definitely keep the Spymaster concept in my hat for later though, especially once we know a little about what future DLC will bring. For now, though, especially with Beast of Winter coming up, I think a character dedicated to unraveling (And creating!) mysteries would fit in really well.