So my truck, a 96 F250 460, has died on me twice. Once when I was going up some dirt hills over the summer, and again a couple months ago in hot stop and go traffic

What I know:
When it dies, it starts to lose power and sputters to a stop
Weird thing, when I turn the key over I can hear the fuel pump powering behind me, but it's easily two or three times as loud as normal
I'll then try and start it. Sometimes it will take (and stay groggily running for about 10 seconds), or it won't start at all
If I let it sit for a while, I'll turn the key over (and the fuel pump sounds normal) and it starts up strong and can continue driving as if there was no problem at all

When it died in the hot stop and go traffic, I got it towed home by a nice passer-by. When I got it home, I popped the hood, and noticed some fluid sprayed on the driver-side of the engine bay. Looked to be red (transmission fluid??) Not sure why the transmission overheating (if it is) would cause the truck to stall though

Does anyone have any ideas? My roommate was thinking that maybe some filter in the transmission cooling got clogged, overheated the transmission fluid, and then it found a way to spray out into the bay...

What I've done:
Banged around the fuel tank to make sure no debris was clogging anything
Took off the distributor cap and cleaned debris of that
Tried some of that fuel additive cleaner to clean out the injectors
I don't know the term, but my roommate pushed on a small injector button along the "fuel rail" above the engine and fuel sprayed out (he says that fuel pressure is fine)

I'd appreciate any tips or anything I should look into!