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JoshI tend to attempt to build sets that are extremely difficult, so it isn't over before it begins so to speak... In the past when I have built a relatively common set and willing to accept EX-EX/MT cards, and I'll classify that as any set where the majority, if not every single card, are available at any given time on eBay or for newer cards can be easily acquired by busting packs, and there is that much access and the only real limitation is funds, it just never felt very rewarding of an experience after I had finished.
Ideas for excellent baseball sets that would require some work from that era that aren't overwhelmingly huge - '55 Doubleheaders, '55-60 Armour coins, 1960's Kahn's, 1960's Bazooka's...