There are currently several opportunities that could help you move up the racing ladder:

2009 Jetta TDI Cup - A really promising series for up and coming drivers. The prize for the championship winner is $100,000 towards a professional ride. My understanding is that they pick 100-120 finalists and evaluate them in a multi day test. However, to attend the test, you have to post $25,000 of the $45,000 full season bill, which is then returned if you aren't selected as one of the 30 final drivers.

Rally Drive USA - Essentially you pay $700 for two days of rally driving school (this usually costs several thousand dollars according to the retail price listed on their website), they then pick the top 32 drivers to advance to the next rounds, and everything is free from there! The winner gets a ride in a 2009 SCCA rally.

Setup season 3 - Reality show competition on SpeedTV. I believe the winner in the past has gotten a ride in grand-am cup/koni challenge. I read the winner of season 3 will get $250,000 for a ride. As far as I know, there are no costs for the contestants besides travel and lodging. The application is still up on the site, but I'm not clear if the selections are complete, or if and when the filming will take place.

Skip Barber Karting Shootout - An annual contest and the winner(s) get a full season in the Skip Barber National Championship. Of course, you have little chance of getting selected as one of the 50 finalists unless you've been karting at a top level for years. Currently, the 2008-2009 shootout has just been completed.

Some of these have different requirements, for example, maximum age. Follow the links for more information on each.