I've been on this server since 2020, and honestly, I've seen them loosen restrictions to the point where Los Santos feels like Harlem in Chicago. You can get robbed anywhere, in broad daylight, with little consequence. If anything, legal roleplayers face much stricter roleplay restrictions than illegal roleplayers.
I don’t disagree with the rules because they provide a sense of realism. They’re there to imitate real life as closely as possible. GTAW is one of the few, if not the only, servers on the Rage MP platform where you don’t see 24/7 cashiers driving around in supercars. That level of economic and roleplay enforcement is what makes it unique.
Not to mention, the staff team is generally very accommodating. It really depends on which admin you talk to, but many of them are willing to help hone your roleplay to help you get to where you want to be. Everyone struggles initially to gain ground—that's what the grind is all about.