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You really, really, really want to think about the OD upgrade right now...you get a gasket set, a new main shaft, needle bearings, syncro hub for 2/3 syncro, 5th gear and sleeve for needle bearings on main shaft, and 5th counter shaft gear. Not sure you need a new 2nd...
Maybe as simple as a bent shift fork from previous attempts to get it into second? Ideally, you could swap tranny tops with a known ok shifting transmission and see if yours performs better with a new top.