Can't start again

My '89 F250 Straight six doesn’t seem to want to start again. It always starts up right away when its cold, though it often takes a push on the gas pedal. The problem is when it’s hot, even a short trip down the freeway, or a bunch of running around town, it won’t start. The starter cranks but the engine won’t fire. The guy I bought it from said it just needed gas when it did that and I still try pumping the gas as I crank it and don’t know whether that actually helps. It always eventually starts, usually within 5-10 minutes, but sure is annoying. Any thoughts on how to trouble shoot this, I have tools, but am not savvy on electrical system testing.

That’s a fuel injected engine so pumping the “gas pedal” is more like pumping the “air pedal.”

The next time this happens, just floor the accelerator and hold it there while you crank it (basic flood clear). If that gets it running then check for leaking fuel pressure regulator or fuel injectors.