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runscottN172 Old Judge or N162 Goodwin - I like them both, and they are so different that I think there's more than enough room for both. I only like the N172's that have clear photos, not those faded blurry ones.
T205 or T206 - I'm finally bored with t206's and starting to pick up a few T205's (I especially like the AL design), but the T206s will always be great.
E90-1 American Caramel or E95 Philadelphia Caramel - E95's, hands-down. The Cobb is one of the greatest cards ever.
1914-15 Cracker Jacks or T204 Ramly - Cracker Jacks are much more interesting. Some are ugly, some are incredible. The HR Baker and Cicotte are my favorites (and I finally have both!)
1911 Obaks or 1912 Home Run Kisses - OBAKs, OBAKs, OBAKs. Too bad there wasn't a ML issue designed like these. All three years are slightly different in design/feel, but they are all top-notch.
1933 Goudey or 1934-36 Diamond Stars - I prefer the '33 Goudeys, but DS's are nice too
W514 or W517 - I thought you said this was a thread about 'cards'? 
T207 or M116 Sporting Life - T207s, though both are ugly.