If there's no black smoke coming out of the tail pipe after it warms up, then it isn't running rich. (A reason why it would be flooded) So I would generally rule out a leaking fuel pressure regulator. Besides, if it was a leaking regulator, it would be harder to start the longer it sits, not the other way around.
I'm not exactly sure, since I haven't worked on an HEI ignition in so long, but you should have an "Vacuum Advance Diaphram" on the side of your distributor.
Sometimes this thing will get corroded and stuck open, which will advance your timing (And raise your idle). And if your timing is advanced when the engine is cut off, it will certainly make it harder to start.
Do you have a hand vacuum pump? If not you can rent one from a parts store.
With your engine running, disconnect and plug up the hose that leads to your vacuum advance canister. Then connect the vacuum pump and apply 10-12 Hg of vacuum. This should raise your idle slightly and you'll hear it. (Usually you want to connect a timing light and measure the advance. But for the sake of keeping it simple, you just want to verify the advance isn't stuck)
If you'd like to check your timing at this moment, you sure can. But you'll also have to rent a timing light. And I'm not exactly sure what your initial timing should be (6-8 degrees BTC), so you'll have to look that up.
Saturday, January 23rd, 2010 AT 8:15 AM