Chiming in with my ass hair experience: Shaving the hair on the cheeks can make you really prone to in-growns, so I recommend just using an electric trimmer there. When it comes to the hair in the crack my preferred solution is to use an epilator. This can hurt quite a bit the first couple of times and some of the angles are tough, but it lasts longer than shaving and never gives me an itchy butthole like shaving does.

Other options include creams like Nair or Magic Shave Powder which last longer and give smoother results than shaving, but you do have to be careful of burning yourself. I have never tried waxing, professional or at-home, but I imagine that it'd be similar effectiveness to epilating, but faster and therefore a bit less painful.