hmmmmm, good questions.
If i were you, i would see a professional waxer who would be able to answer all those questions AND give you an amazing result.
Women see waxers all the time for even the most intimate of waxing services and men are clients more and more often nowadays for their back and butt hair . . . you should think about seeing one yourself.
For a session that you would need, it would probably be about $55-$75 dollars and would last five-six weeks of being hair free. It also doesn't hurt as much as people think it does . . . fairly painless with amazing results.
Sweetpea