Do you have an inline pressure gauge connected so you can monitor fuel pressure as it misbehaves?
I once spent a YEAR troubleshooting a dying 460 in my old Mercury (granted it sits in the garage & I didn't get to it that often). It would die after it started to get warm, then I'd have a hard time restarting it. I dicked with it forever, changed the pump, rebuilt the carb, then I decided I was going to pull the tank & see if there was some shit in pickup sock. As I'm pulling the rubber fuel line off the tank I notice that the line was wrapped up & over the spring perch... The year before I got some new exhaust welded up & the guy moved the fuel line out of the way so he could fit new pipes & never put it back. It was bent perfectly so that when it was cold the ID of the tube stayed open, but as soon as the exhaust got hot it would warm up & kink completely.