Brian:
I've only been collecting for a few years, so I don't have as much experience as most, but I agree with Jesse that a T206 is a great place to start. Other than the big names he mentioned, you can get some very nice examples of less mainstream HOFers (think: Tinker, Evers, Chance, Crawford, etc) for under a couple hundred bucks. I might also suggest trying some of the other popular pre-war issues like 33 Goudey, which, in my observation, doesn't attract as much attention on this board. 1941 Play Balls are a great place to look as well. If you're looking for something a little more "B-side," Delong, Diamond Stars, or some caramel cards could be an option. Finally, if you're interested in bigger names on a budget, Exhibit cards, IMO, are a great value.
Best of luck. Pre-war baseball cards are so rewarding in my opinion.
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