A good all around tranny and easy to find and cheap- TH350 (Turbo 350) It is all I have ever ran behind a small block. I now run an external cooler instead of running the lines to the radiator, this makes the tranny run cooler, espically when pulling a load like I often do. I bought a nice cooler for $35.00 and you can go up from there. They even sell them with cooling fans if you want to go that far.
Gas is getting pretty spendy these days. I put a 700R4 in my 66 and it's a world of diffrance. The old TH350 ran high RPM's (around 3000 at 70MPH) and now purr's down the highway (around 1700 RPM at 70MPH). Check out www.bowtieoverdrives.com for ideas. They have fixed the problems with the early 700R4's and made them tougher.
I'm running the factory 4:10 set up. I got the tranny from mad dog transmissions. You can find them on E-Bay. You will need to have the drive shaft shortened but other than that it all bolts right in. I also ordered the install package that comes with TV cable, TV corrector bracket, and dipstick. So far Iv'e have no problems with the tranny. It has alot more snap than the old TH350 it replaced. It chirps the tires when it hits 2nd and 3rd. I only have a stock 283. Not exectly a powerhouse but hopefully soon it will have a mild 350 under the hood.
Yea, i have a stock 283 in there too with a powerglide, i know what you mean. i cant wait to get a 350 with the 700r4,