CK5
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will my TH350 bolt up to a newer 350 block?

Yep, but you'll need to use a flexplate that's made to fit the '88. The bolt pattern on the crank changed when they went to the 1-piece rear main seal. There are 2 different diameters for the torque converter bolts, so you'll need to check that. Most aftermarket flex plates have both patterns drilled so they'll work with pretty much any GM torque converter.
 
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