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My mother in 75 bought and use to own a 74 Monte Carlo S, all original California factory 350 V8 4bbl,ran good for about 6 months then began having issues with not wanting to start at times. Her car would run fine after being warmed up like any old carburetor vehicle when cold,but would always give her issues with trying to start after being driven a short or long distance and being turned off and sitting for awhile or few minutes,the motor would just refuse to start acted like it was flooded out real bad.Sometimes after a good amount of pumping and cranking it would finally start and sometimes it just wouldn’t and she would have to leave it where it was parked and have it towed to the shop.The issue always seemed to be something to do with the distributor not so much the carburetor being bad or the fuel line not getting gas to the motor it would pick up the fuel just fine when you would try to start it.She kept it maintained but no matter how many times you put in the shop it would act up again with not wanting to start,these are good cruisers,big and strong can take a beating,great bodystyles but would say not the best nor dependable chevy’s to own unless completely restored and tweaked out. IF ANYONE OWNS OR HAS OWNED A 73-77 MONTE CARLO IN THE PAST THAT GAVE YOU THE SAME ISSUES WITH STARTING I WOULD SURE LIKE TO HEAR YOUR FEEDBACK,STORIES AND ANY INFO YOU CAN GIVE ABOUT IT WHAT YOU HAD DONE TO CORRECT THE PROBLEM ETC PHOTOS OF THE MONTE CARLO ARE WELCOME ALSO HUGE FAN OF THESE CARS AND BEEN WORKING ON THEM SINCE JUST WOULD LIKE SOME INSIGHTS FROM 73-77 MONTE CARLO OWNERS.

Difficult hot restart sounds a lot like vapor lock. I’d like to think today’s best and brightest could diagnose this, but admittedly a carb is a uncommon sight these days.

Curious why you don’t feel it’s fuel-related? Ignition woes can surface when hot, but it’s not a start-only issue.

Look for missing heat sheilding of the exhaust and fuel lines. Replace any that is missing; possibly add more for good measure. Test, adjust as necessary.

Sounds like a choke issue to me. The choke is adjustable served by a temp sensitive spring,

Agreed with meanjoe75fan and Barkydog. A car this old may just need a carb rebuild by now. These are very simple engines and there isn’t much to troubleshoot. You need gas, spark, and both occurring at the right time to start and run. You can pretty much rule out timing and the other two are easy to check for.

If it won’t start when hot, give it a shot of starting fluid–if it fires right up, you know it’s fuel related. If it doesn’t and has the GM HEI (early electronic ignition), and you verify there is no spark, I’d start looking at the pickup coil and module in the distributor.

As a side note, a guy at work has a beautiful, bone stock green 1973 that he drives when the weather’s too bad to ride his Harley. I cringe at what the road salt is doing to this nice old car.

Agree with @oblivion here. These vehicles had an ignition module in the HEI distributors which would malfunction when the engine got hot. The cheap silicone grease (used as heat sink) would melt and run out from under the ignition module. I found that using silicone sealer (GE) usually fixed the problem.

I owned both a '72 and a '74 Monte Carlo at various times; both with the 350/4 Barrel.
Offhand the problem sounds like it has to do with the choke. You state it was a 4 Barrel so that means it was a Quadrajet and if not a choke issue it could have been related to the jet well plugs leaking internally. That will cause a flooded condition after the engine is shut off.

If you’re convinced it was a distributor issue then that could have been due to the contact points closing up due the distributor cam not being lubricated, an advance plate sticking, or the contact point wire being rubbed through due to movement of the advance plate.
The '74 Monte Carlos should have point distributors like all other GM cars of that year. From memory, I think the '74 Cadillac El Dorado (?) was the only model with HEI in '74.
It was '75 before HEI was fitted to all of them.