the short version is yeah i think annabeth is so much more of a rulebreaker than percy :’D
at least in the intentional sense? percy starts off the whole series talking about how he never asks for all the trouble he gets into, and he doesn’t like it. he doesn’t want to keep getting kicked out of school and fucking up. he hates being branded a troublemaker.
annabeth on the other hand sat at the poseidon table to talk to him while he quietly freaked out a little. she brought four people into the labyrinth despite the usual three person to a quest rule. she snuck into his cabin while he panicked, like you mentioned! annabeth sees the rules and she isn’t afraid to bend or break them if she thinks it’s for the best. percy sees them and he’d prefer to work within them, but his life doesn’t usually let him do that. i wouldn’t say he’s 100% opposed to rulebreaking, because he’s got definite issues with authority too, but he’s not a purposeful troublemaker. percy seems to break the rules or get in trouble for the sake of other people, which fits right in with the whole loyalty as fatal flaw thing, and gets worse the more he cares about someone. he challenges the rules when it’s unjust and calls them out moreso than just… casually breaking them.
annabeth sees the rules and disregards them if they don’t suit her. she is more confident in her ability to wiggle around them. (which similarly could be tied into her hubris.) there are certain customs and practices she might adhere to (especially when she’s younger), but i feel like she’s more open to saying ‘fuck this’ than percy is. she cheats when they’re competing! when they’re sparring or racing or w/e, she will do it happily. she’s more likely to drag percy into something that’ll get them in trouble than the other way around, imo.