On skill levels vs rolls, I feel it might be worth trying to combine the two? If a player isn't at the required skill level, they can give it a shot - story-critical checks could have alternate paths as a precaution, even if they're only accessible after failing the checks. This would require a fair bit more planning and writing, but it can feel a whole lot more natural than just gating a player.
Basically, just treat checks as both a writing device and a means for a player to exert some agency. Get silly with it. Poke fun at the situation if the player digs themselves into a particularly unlikely hole.
Also, hell yeah trans rights!