Here's what I'd do (as an MC), but this solution isn't for everyone...
Underdog (Chopper Playbook Mod)
When your gang isn't the biggest, baddest, or most well-equipped in town, you get the move "Something To Prove". After you have that, you can also take the rest as advancements.
Something to Prove: At the end of each session, instead of saying who knows you better, ask the other players as a group if you proved to someone this session that you're a force to be reckoned with. If the majority agree you did, every PC knows you better (and takes the appropriate +1-Hx) and you mark XP.
Recruits: At the start of each session, if you proved yourself last session, you get a few new recruits (maybe only one or two, but given time it'll add up). These might come from another PC's gang or followers, or else from the general population, MC's call.
Fearless: When you or your gang is outmanned or outgunned, you (or they) get +1-armor.
Never Give Up: When you'd be out of the fight, like unconscious, dead, or captured, you can instead take a debility (and set yourself to nine o clock, if you're higher), but only once and only in a real battle. If your gang sees you do this, they'll of course fight to the death if you ask them to, but only right then and there.
Why, you might ask? It turns a fictional and mechanical weakness into a potential strength (fearless + never give up), aligns your own real-life concerns with those of your character (something to prove), gives you an additional XP source to help catch up in advancements to the other players (something to prove), possibly drives pc-npc-pc conflicts (recruits), and more.
I actually think it's a pretty tidy solution!
- Alex