GLad it's solved. I just want to add for any future folks looking at this thread. I'm not sure if the 4wd and 2wd front calipers share a similar design but if they do, don't even think about rebuilding them!! Well, at least that's the consensus I came to online. I have rebuilt a few calipers before and never had an issue. Well, I tried rebuilding those on my Dak and I spent so long trying to get the dust seal to sit correctly. Apparently I'm not the only one and the general solution was to give up and bite the bullet for new calipers.

Others may have better luck than I, but for anyone who isn't interested in messing around, just get new calipers.

 

Just had the same issue with my 99, replaced everything in the front brakes. Also had the same thing happen on my 92 last summer. Same solution. I have had 6 of these trucks and wrench for a living. Dakotas and Durango's are among the few types of vehicles on which I have yet to have to replace a master cylinder. I'd say a bad mc is unlikely
On my 99 the past owner had just had it in the shop where they replaced the pads and rotors 500 miles earlier. I had to replace them again, warped the new driver side rotor badly and cracked the pads all to he11.