So, you have roughly 80,000 miles on the trans now, have you changed the fluid since the original install?
I believe I would start with resetting the kick down cable, probably won't help, but its pretty easy and may help with the problem. Could be an issue with the cable & linkage not moving like its suppose to, since its mostly driven in the salt & slop now.
I have a 96 Dakota 5.2, 4x4 stuff in my 49 that originally had 44,000 miles on it (now has 63,000 miles on it). When I use the truck, I back it out of my driveway, then shift it into forward to drive away. I have found that it doesn't like to go from reverse into drive and pull away as soon as it grabs. Almost every time I do a fast direction change and want to drive as soon as it grabs, it messes up the shifting. It wants to hang in 2nd a lot longer then normal. If I pull over, put it in park, shut it off, then restart it and put it into drive and wait a couple seconds before moving, it shifts well.
I have read that the speed sensor at the tail end of the trans determines the up shift rpm. I don't believe Mopar units are available any longer, so maybe when the aftermarket speed sensors get older, they don't function so well. There is also a relay in the under hood fuse box that controls the OD and the solenoid pack in the trans (mine was labeled on the box cover as a fan relay instead of a trans relay, the only thing that used an electric fan was the 4 cylinder, that is an early production 96 deal). Maybe that relay has some corrosion on its terminals.