I would do an "auctions only" ebay search for either Cobb, Young, and Mathewson cards. (Although I would definitely add at the minimum Walter Johnson, McGraw, Speaker and Lajoie).
Pick one of these players and follow some of their graded cards in your "watched items". Get a feel for their prices. Follow only graded examples by PSA or SGC with a common back such as Piedmont or Sweet Caporal. If you buy graded you will avoid fake cards and difficult to see condition faults. After several weeks of this, you'll have a good idea of the prices. Having watched several auctions to completion, you'll have the price info you need and you can bid away. Keep in mind these are the most popular T206 cards so you might have to bid very late to get a good deal.
The red background Cobb is much cheaper than the other Cobb variations. The other pose variations don't have as much of a price difference.
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