oil cooler is not going to help with cranking. It is pretty amazing how fast oil cools with the engine off. My air cooled vw, (only oil temp gauge equipped engine atm) drops 20-25° in just 5 to 10 mins.
An oil cooler will help if your oil temps are running over 240-250° and pressure is dropping while driving.
Is that starter you have clockable ? As in can rotate the motor part closer to the block ? If it is I would start with that getting the solenoid and motor part as far from the header tubes as possible.
I don't think the oil cooler will help either. But I'm running out of ideas here.
Checked compression
Tried every possible timing setting
Tried 3 different carbs
Tried complete brand new distributor
Tried Checked the plugs for proper type/condition/gap
Checked for intake leaks
De-carbon the cylinder multiple times
Flushed the cooling system 8 times
Tried all the possible settings and configurations on the vacuum advance
What else... There is more, I'm sure.
ONLY cranks slow or stops turning over when it has spark. ONLY cranks slow or stops turning over when the engine is hot.
I have the starter clocked away as far as possible, with a fab'd aluminum heat shield protecting it. The rig had the same issues with the stock starter. I don't think its the starter, but I could be wrong. Removing the Thermostat eliminates the issue, which would have minimal impact on the starter temp, I assume.
Since heat is the only thing I have left to try, all I can think of is cooling the oil down. I can t cool the engine down any lower than it is. Its already running too cold as is with the 160 T-stat.
Normally I use 87 octane. I just put a fresh tank of 92 octane fuel (30 gal) with enough octane booster additive to treat 40 gallons.
Too soon to tell if that helped. Its not starting perfectly, so there is still an issue. I will have to drive it more to see if the worst of the symptoms are gone with the octane thing. It take a lot of starts to finds that "sweet spot" in temp and time for it to not start at all where it just grinds to a super slow crank.