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If I continue to turn it counter clockwise, will the drive train tighten up and catch even in the opposite direction, and
will I hurt anything by loading the engine components in the opposite direction

Naw, you should be fine. If you block the wheels well and put it in 4th gear nothing should move that much. Just remember to get it set back to TDC for the 1st cylinder after you pop the crank bolt loose.

erick

85 Pickup
33s, lift, EB cam, header, exhaust...