Depositing without middle man?

Has anyone had experience depositing money using bank drafts or cashier's checks? I want to do this for two reasons:
1. Open up a new account with a different username so I can get rakeback at a site I already play at (Edit: I don't want to talk about rakebacks, I know this is a 'no rakeback zone', I just want to talk about deposit methods)
2. Give a belated Xmas gift to a friend

My real question is, will they need my name & address, and will they verify it against existing accounts? If they do, that would make #1 difficult because I already have an account and I know most places frown on dupes. It would make #2 difficult because I'm putting the money in another person's account.

Is there an easier way to do this?