First Gen starts rough after sitting for SHORT PERIODS only

Hey guys. I've got a '97 Tacoma 2wd with the 2.4l, 4cyl engine. It's at 270k at the time of this post.
I've been chasing this rough start issue for a long time. Everytime I try to fix something, it seems to help a bit, but never totally goes away. I'm sure many of you have been there.

At this point, what happens is this: it cranks for a little longer than normal, but otherwise starts fine if it's been sitting overnight. It's also fine if I start it after it's been sitting for only a few minutes. BUT, if it's been sitting in the parking lot for 20-60, it will be hard to start and run very rough until I get a change to drive it around and work out the problem. Naturally this means I notice this issue mostly while trying to take it on errands.

Up to this point, I've tried replacing the fuel pump, cleaning the fuel injectors, replacing the spark plugs, cleaning the intake manifold and throttle body, and replacing the catalytic converter. Like I said, some of it helped, but this is where we're at with it.

I have a few ideas of what could be going on at this point, but I curious to see if anyone else has had this specific problem. The timing of when it happens seems very odd to me.

 

Try searching “hot no start condition”

took me days to research
Injectors cured my issue

 

Could be a leaking head gasket. Coolant gets into a cylinder and it’ll run rough until the coolant burns off