Head of Guild stuff...I'd like a fresh take from a up-and-coming writer for this. Don't know if I care too much about political aspects of the job, but he could go around as an enforcer, taking out the bad actors in the Guild. He just needs a foil to join him. And a cat-sitter.
I think it'd be in everyone's best interest to stay away from everything related to the cats. Instead of it being a small piece of continuity for the character - current-day writers are literally using them to slight Gambit and as an excuse as to why he's not in any action. Cats aren't helpless children. You leave them alone in an apocalypse and they'd outlive every single one of us. They should be allowed to roam free on Krakoa without fear of being preyed upon - but that place is so inconsistent and weird, I could see them suddenly disappearing too.
My vision for him being involved with guilds would completely remove him from Krakoa. Obviously, seeing as they haven't come up on the Krakoan radar, despite their underworld/black market roots, there's enough going on that it wouldn't need to be tied together. I wouldn't want Gambit stuck behind a desk or sitting on a throne any more than I want to see him running around in fairy-land. There's no way it's being run the way he'd like it to be - in terms of jobs and those who are overseeing it. I think we'd get volumes of Gambit just going around and "taking care of" trouble within his ranks while trying to avoid being literally stabbed in the back. And because it's an international affair - he'd be globetrotting, most likely with a small inner circle. Very Jason Bourne/James Bond/ Burn Notice style of action and intrigue. This obviously doesn't seem like CCs style though. He's much more standard superhero stuff.
I'd take a fresh take on it as well. Fabian could have swung it. Cates was another top choice - but I'd also welcome Asmus back with open arms.