I'm more worried about the tax man, that's the big thing for me... "where is this money coming from". Idk, just report it as income? I want to eventually live off the grid so I don't want to invite any trouble.
Bitcoins are not tax exempt in the U.S., Canada, and other countries. Google "bitcoin tax reporting" or something similar and you'll find more info.
If you're selling a *lot*, you may wish to consider an accountant. It will cost a few hundred bucks, and he/she will do all the necessary paperwork for you.
I just worry about if I pay off too much at once, does that throw up any flags to have me investigated though? I've still got time before I finish with school but I'd like to get on with my life and not be worried about being in debt... maybe I am just paranoid haha.
you should sell in smaller amount at a time.
That can still be illegal.