Ok so it's been months and I haven't figured it out yet. I haven't spent much time maybe 2 hours total actually diagnosing since it's a weekender and not a daily driver but here's the situation.

1986 Mustang GT T-Top
Starts up cold perfect.
Once it gets up to temp won't restart, acts flooded
Compression is good 165+ all across when hot

I Unplug the fuel pump relay and spin her over for a few seconds and she starts right up with a puff of black smoke like she's flooded

I didn't know the age and condition of the fuel injectors so I put a new rebuilt and bench flowed set in there. The car runs much smoother, but the problem is still there.

New parts fuel/ignition related

MSD Cap
Rotor
Ignition Module
Fuel Pump (255lph)
Fuel Filter
Ford 24lb Fuel Injectors

it's a 24lb MAF converted system with a pro-m calibrated MAF Cobra upper and lower intake and not much else

Any ideas?