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You should seriously consider Wrath of the Lamb. The challenges let you get to grips with some of the rarer items early on, so you can use them better when you do find them.
Samson's pretty cool.
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I want to at least beat It Lives once before I get the DLC. I might also try for Sheol as every character, but I don't really know how viable that is. Magdalene is so weak at the start of a run that I usually get impatient and make lots of devil deals, ending in my death even with the Yum Heart.