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T206Collector...I may go after the T-306 set, especially if there's a green Cobb in it! 
My first "vintage" card would probably have to be a 1933 Lefty Gomez I got for fifty cents in a bargain box at a card store back in the late 1980's. It was heavily creased in the middle, but presented well otherwise. I sold it in the early 1990's for about $15, if memory serves me. I also remember being excited about adding a poor condition 1960 Topps Stan Musial to my 1987 Topps and 1988 Donruss collection. I also had a caramel card (don't know which series, but might've been E92 Dockman) of Bender for awhile.
But my first T206 card came in 1997 when I bought a Matty White Cap and Bender Portrait for $500. The Matty is now in an SGC 60 holder and the Bender is in an SGC 50 holder. I still have em and ain't ever letting them go.