I've been collecting prewar for about 15 years now. Before that it was modern growing up in the early 90's, followed by SLUs, and then a little postwar. For me, I was always drawn to getting stuff other people didn't have. I quickly found postwar (50's and 60's Topps in particular) were really common. That pushed me to buy my first T206 but after a few months, again, I came to realize I could pretty much buy any T206 on Ebay at any time if I didn't care about the back.
Eventually I started working on an E93 set and still recommend that set most of the time for those jumping into prewar. It is a smaller set (30), packed with HOFers (18 I believe), and the set finds a decent balance between being too easy and too hard. Price wise, it is also within relatively cheap to complete, though prices have increased for the key cards. HOFers though are generally in the same ballpark as their complementary T206.
I've since gone a bit off the rails and keep trying to build sets that are nearly impossible. 
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Current Wantlist:
E92 Nadja - Bescher, Bridwell, Cobb, Donovan, Doolan, Doyle (with bat), Lobert, Mathewson, Miller (fielding), Tinker, Wagner (throwing), Zimmerman
E/T Young Backrun - Need E90-1, T216 (all versions)
E92 Red Crofts - Anyone especially Barry, Shean, and Evers
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