I talked to a guy that owns the local tranny shop at a cruise night last year and he said that based on what he sees coming through his shop current mopar trannies are no better or worse than anything from Ford, GM or Toyota.
Anyhow I have had two Dakotas the first one an 89 had an A500 and the only issue I had in 256,000 miles was a shudder when I put Dextron in it instead of ATF 3 and the rubber hose connecting to the radiator cooler started leaking around the crimp to the hard line.
The current Dakota is a 99 with 165,000 miles has a 44RE. I have had to replace the output sensor ($11.00) and the govenor control solenoid ($35.00), neither of these issues left me stranded they just caused the tranny to act pecular until I changed them out. I do get a little flare on the 2 to 3rd shift on hard acceleration when the outside temp is around <=20 and the tranny is cold. I just have let it warm up before getting on it.