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TbobN172 Old Judge or N162 Goodwin- Old Judges are pretty drab in appearance. Not a 19th century guy but I'll go with the Goodwins.
T205 or T206- T205 hands down. The American Leaguers may be the best card "subset" ever produced in terms of color, eye appeal and aesthetics.
E90-1 American Caramel or E95 Philadelphia Caramel- Depends on condition. In higher condition the E90-1s can't be beaten.
E120 American Caramel or E121 American Caramel- Toss up. Don't like either.
1914-15 Cracker Jacks or T204 Ramly- Ramlys are so ornate, I give them the nod.
1911 Obaks or 1912 Home Run Kisses- Not even close. The Obaks are undervalued, underappreciated and just plain great. Personally I like the 1910s better than the 1911s but the '11s are still nice.
1933 Goudey or 1934-36 Diamond Stars- Goudeys although I collect neither.
D304 General Baking or D322 Tip Top- Close, neither set does much for me, I guess I'll go with the Tip Tops.
W514 or W517 Who cares?
T207 or M116 Sporting Life Man, can't believe you guys are dissing these 2 sets. Check the buy/sell prices on these cards compared to the buy/sell on the (non T207) tobacco and caramel cards and come back in 5 years and I think you'll be floored. Both of these sets have huge growing room for investment. The scarcities in these 2 sets are incredibly tough, especially the M116s which seem to NEVER pop up. The T207s are surrealistic, moody, dark and beautiful. They belong in the Louvre while the other cards T201 through T216 belong in the local art gallery. Sporting Life cards may be muted in color but nice examples are gorgeous. Nothing beats a T207, though, except maybe a violet E94 