With either the early pre-96 or late model 99+ m5odr2 transmissions mated to a 302 you need to use all 1995 F150 parts to install it.
Block Seperator Plate
164 tooth truck Flywheel (not a 157tooth 5.0 mustang flywheel)
Clutch Kit
MANUAL Starter
Your issue lies in using an automatic starter or wrong block plate that locates the starter.
The auto/manual starters have different nose depth and the 2 block seperator plates have different starter mounting positions
Honestly, that's exactly what ended up being the issue.
They were trying to use stock Ranger starters, twice. A mustang starter once. Finally got a F150 starter, he cranks up perfect every time now.
However...
Now I have a fuel/ignition issue.
Cylinders 2, 3, 5, and 8 don't seem to be firing.
Just discovered this problem yesterday, been screwing with it for a while.
Thought it was a fuel delivery issue, so I dropped the tank, removed foam baffling, cleared fuel lines, replaced pre-pump filter. Opened the electric pump, vanes and rotor look fine, not much debris on the internal screen.
Put it all back, started her up. Getting 5.5-6.2 psi consistently.
I'm now looking into carb or ignition issues.
Attached photos of the set up...
I feel dumb with carb situations, but I'm sure we'll muddle along and eventually get it in time for something else to fail.