Thanks to all for the replies. Major update:
I sat down a few nights ago to put together a spreadsheet of how much all the necessary parts would cost, if I replaced everything discussed, before machine work, and the numbers got REALLY big really quickly. The numbers included heads, intake, lifters, rockers/shafts, stroker kit, oil pump, windage tray, pushrods, cam, lifters...the whole 9 yards.
I decided to see if I can find a 440 with better heads for a reasonable price, since it would get me on the road faster, for less money, with a faster car, and I can stash the original motor for later if I really wanted to keep it original.
So...I pulled up Craig's List, and one of the first postings I saw was for a newly rebuilt, still in the car, running and driveable 440 with a stout street build. I took a few hours yesterday to go see the engine/car Owner says that it was a low mileage (50K) 440 out of a 70 Imerpial or NY. The motor is freshly built with about 100 mi on it, and it's sitting in a 67 GTX. The block and crank are still standard size because he said that the motor was very well cared for and everything was at the very low end of spec. Motor has a Hughes Cam, Performer RPM manifold, a custom built Holley 800, headers, chrome box Chrysler electronic ignition, and 906 heads. The motor is very nicely set up, and no corners appear to have been cut. He's got most of the receipts for the work. It started with one flick of the key, has a nice lopey idle, no smoke, ticks, knocks, or funny noises. He took me for a ride. From a slow rolling start, it broke both rear tires loose, snapped my head back and pushed me about 4" into the seat. It ran at a steady 175 degrees the whole time. The car had a manual valve body automatic and 4.10 gears in the rear, so I wouldn't expect it to do the same in my car, but the motor appeared to be very well built and it ran like a scalded cat.
His price for the entire motor is less than the cost of about half of the parts for a stroker 383, forget any machine work. I cannot think of a reason not to pull the trigger on this one, so I did.
Without getting into (more) detail, he offered to put in a valley pan that blocked off the exhaust crossover, said that it would give a few more hp. Yes? No? Any reason not to do it?
Second question - the carb is fully tricked out Holley 800. It's got purple billet metering plates, no choke, dual feeds, and a bunch of stuff I probably don't know about. He offered a Carter Thermoquad because it might be a bit more "street friendly". The car ran like a rocket with the Holley, and I have ZERO experience with the Thermoquad, so should I consider it?
Thanks...
Chris