A VW convertible is a good way to start. They're heap to pick up and relatively cheap to redo and have a high desirability (they sell for more than a hard top). You can redo the VW as a stepping stone onto bigger and better things. It's pretty easy to redo a bug for 2000-3000 dollars and if you do it right you should be able to get 6k-8k out of a convertible. Use 3-5k or so to pick something up and then you have some start up capital.
1985 Ford F-150 ex 4x2
NOW: 300-6, D44, spooled 9", T-18, twin stick NP205
Show: 1966 VW Beetle Ruby Red, retored stock (see avatar)
Just your average 18 year old. . .