Are they a headache as a daily?
Depends on the initial condition of the vehicle when you purchased it. Then once you have purchased it, depends on how much you are willing to sink into it to fix/improve it.

Boring vs Sports?
I'm looking at 50K~70K range car... while looking at new options like those Protons.. Almera.. etc... my "high-school me" thinks.. what about those legendary RWDs? they're fun and rare

Its a subjective matter, what is your objective in the first place for the vehicle? How much cash do you have to purhcase?, how much money are you willing to put into the wear/parts/repairs?, do you have an alternative mode of transport incase the car needs to sit in the workshop?