I am removing an 88 TBI 305cid and installing an old style 2 piece rear main seal 383cid. Am I correct in considering the following?
1. I will need a flywheel to fit the old style crank but the tranny will fit pilot bushing of any year. It is a 5 speed manual. Pressure plate should bolt onto old style flywheel.
2. Can I remove the TBI alltogether and run a mechanical fuel pump off the same fuel line, put on an Edelbrock intake and Holley carb?
3. Will the 305 radiator handle a slightly built 383cid?

 

Yes on the clutch questions. A 153-tooth flywheel should do the trick. However, you'll either need an interally-balanced 383 crank, or an external balanced flywheel.

If you remove the TBI, you're best to either use a return-style regulator and run the in-tank pump, or drop the tank and remove the in-tank pump and run a mechanical pump. You could run the in-tank pump, mechanical pump, and return style regulator. Or, in-tank pump, and mechanical return-style pump.

A 305 radiator in good condition should handle a mild 383.