Regardless of your skill, buy a high quality AB (Iwata, Badger, Paasche, etc.) and a high quality compressor that you can buy.
I started with an Iwata Eclipse and an Iwata Smart Jet compressor two years ago and couldn't be happier. One advantage of Iwata is that if Hobby Lobby is near you, Iwata parts, unlike other brands parts, are readily available, and you can buy them dirt cheap using HL's weekly 40% off coupon (visit their web site and print it). Chicagoairbrushsupply.com has typically lowest prices and their service is second to none IME.