Hello Chris,
First off, welcome to the board! You'll get plenty of help from everyone here. The best advice I can give you is if possible get out to a show with some vintage and actually look at what cards you find most attractive and appeal to you. I know it can be difficult to find a decent show to do this, so I would also recommend spending some time going through both the monthly pickup threads here and visiting oldcardboard.com (link at the top of the page). Old Cardboard has a ton of different sets listed and most have galleries so you can get an idea of what each card looks like.
With the limited budget you have, I would look at things like Goudey Wide Pens (R314), Exhibits (w461 for example), 35 Goudey's (R321), etc. You'll probably still need to spend more for top tier HOFer's (Cobb, Ruth, Dimaggio, etc) but many other HOFer's can still be found in your general price range. If I can help you in any other way, let me know.
Best of Luck,
DJ
x2drich2000
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