If you're going to be flying a lot right away, check out the AA Platinum Challenge to get fast-tracked to PLT status. There's a link in the AA forum to FewMiles' AA elite status web site- it will give you loads of info about the challenge and how to do it.

As for hotels, I can't speak to Hilton, but it only takes 10 nights to get to Silver status with Marriott and the hotels are usually decent.

GG