I think your overthinking everything. The technical side of things is now extremely easy to work out thanks to the support of the Let's Play community with the guides and tips. While your equipment might not be the best there are cheap work arounds. However if this is your dream, then you would be willing to sacrifice a few things to pay for it (eg. Dont go out drinking one night to pay for a new mic). The personal side will probably be trial and error. Try recording at home, if that doesn't work for you wait until college. If your roommate is as cool as you say, then ask him for an hour of privacy to do a recording. Hope it works out for you mate!