What should I be aware of when I look at them? I have a Dakota now, and I think I wanna upgrade.

 

Transmision, plenum gasket/spark nock, trackbar/panard bar are the top 3. Search for the subjects and you will find a plethera of info on all of them.

 

Shott pretty much nailed it on the head. The big things with the 2nd Gen Rams are the tranny, plenum gaskets, "death wobble". The 2nd Gen section is literally packed with threads on these items and the 3 guys in this section that you can really get great info from are shott8283, Tani1500, and steve00ram360, the last two being section mods. They are solid trucks when well taken care of and several have seen 150/200k on the motor.

Since you have a 1st Gen Dak, I'm going to go ahead and suggest this as a possible option to you as well. Consider going to a 2nd Gen Dakota. The 97-04 Dakota models had all the same motors that the 2nd Gen Rams had, were bigger then the previous model Dakota, but also were every bit as heavy duty as the Ram 1500's. In fact, my 01 Dakota had more bed hauling capacity then the same year Dodge Ram 1500. Unless you really want a full size, I'd seriously at least consider looking at a 2nd gen Dakota. They're good reliable trucks, had only 2 major issues in the transmission and ball joints, which the ball joints are covered under a recall now, and get slightly better gas mileage while still offering a good reliable work truck.

Either way, good luck in your search!