Yeah, Joss and Jennings are relatively affordable Hall of Famers, and not a bad place to start. I agree that you should try to find a card with good eye appeal for its grade (or potential grade), but you should also get a card that you like. There are a lot of fun and interesting cards in T206, and assuming that you're going to collect at least partly for fun, rather than purely as an investment, you should start with cards that appeal to you.
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