My friend buys a lot of Dakotas to re-sell at his used car lot--about the only issues he's had with them are they have a crappy steering shaft u-joint setup that is very costly to replace and its hard finding good used ones--however,I found him a cheap source online that sells for 150 bucks less than dealer cost...he's bought a few with bad overdrive trannies and replaced them and sold them,Mopar's trannys seem a bit weak compared to their older ones...he's had one that needed a computer,it refused to start on cold days unless you warmed the computer up with a hair dryer first!--I guess them being under the hood on the fenderwell isn't the ideal location for them..
A few others he bought had minor issues like a bad speed sensor in the rear diff,and one had broken exhaust manifold bolts on a 3.9 V6 that were not fun to fix--but all in all the Dakotas sell very quickly and few of them came back ,he has had a lot better luck with them than some of the other trucks he's bought to re-sell,like Rangers and dare I say,some GM's!--the S-10's are hot sellers but seem to have more than their share of problems--usually rotted brake & oil cooler & fuel lines,rotted oil pans,things like that that suck to fix and cost a lot due to "dealer only" parts...
I had a friend with a 1987 Dakota,his had a 2.6 Mitsubishi engine that had a blown head gasket when he got it free...we pulled the head off and discovered the block had a nice groove burned between 2 bores where the gasket failed,so we went salvage yard shopping and found a nice low mileage engine in a Crysler Lebaron K-car for 150 bucks...but when we got it to his yard we noticed it had NO motor mount holes for a RWD application!--the bosses were there,just not drilled or tapped!--we managed to drill the holes and tap them and it slid right in nicely...we always wanted to put a 318 or 360 in it but he liked the fact it got 25+ mpg so he left it stock...
I think they are good trucks--not too big or small,and they seem to hold up pretty well..they dont rot like most others either...one thing to watch out for is the drivers side door hinges like to rip out of the door--they are welded to the door AND the cab!--so repairing one isn't a fun job,and I have seen quite a few that need them fixed...