Prof, the set is called "the monster" for a reason, and, objectively speaking (granted I am biased) it is likely the greatest and most complicated sports-card set extant.
Generally speaking, you can break the backs into several tiers. Here is my take:
Tier 1: Common Backs -- Piedmont and Sweet Caporal (although there are some series and factories in both that are quite difficult).
Tier 2: Less Common Backs: Sovereign, Old Mill, SL OM, Polar Bear (but some old mills are very difficult with certain players/poses and some Sovereigns can likewise be quite difficult)
Tier 3: Rarer Backs -- EPDG, American Beauty, Tolstoi, Brown Hindu
Tier 4: Rare Backs -- Red Hindu, Black Lenox, Carolina Brights, Broadleaf 350, Black Lenox
Tier 5: Super Rare Backs -- Uzit, Broadleaf 460, Drum
Tier 6: Wicked Super Rare Backs - Brown Lenox, Brown Old Mill, Ty Cobb Back
Not every card with every back, and, as mentioned above, some common poses can be very difficult, even in a more common back. Some front/back combos are near impossible and/or the only one known. And sometimes, a rare back is actually fairly common (see Duffy and McGraw Glove at Hip Red Hindu). To complicate things, certain backs has different series and different factories, although the former is much more relevant for your query; Sovereign 460's tend to be tougher than 150-350 (although no portraits) and Broadleaf 460's are much rarer than their older 350-counterpart.
Regarding value, I think its more than just back rarity, but also the rarity of the front/back combo. And, sometimes certain cards and certain backs get hot or cold.
Bottom line, there is a lot to learn and its best to do it organically, rather than rely on a value multiplier. My advice is to buy HOFers and/or rare backs and better and you cant go run in the long run. Have fun!
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