I'll give you that the older Dakotas had problematic transmission to say the least. However if you get one thats 2000 or newer they have a new 5 speed auto instead of the problematic 4 speeds.
I've had mine for 3 and half years and the only things I have done are ALL the fluids, battery, and seat cussion. The ball joints were replaced under factory recall.
Very solid truck, and very powerful, with not bad milage.
If you are looking more for an SUV, my mom has had 3 Jeep Grand Cherokees since '99 on a continuous lease. She doesn't know what else she'de have. They also have the new 5 speed autos and QuadraTrac four wheel drive systems. The ride is nearly unbeatable.
A dealer can also ussualy work out good payments if they want your business. I got my truck nearly 4 years ago for $17,500. I was able to work up a $4,000 down payment and got a $250/mo payment at 6% intrest. It was a 6 year loan, but make higher payments when you can...mine is almost paid off.
Also dealer cars ussualy come with a 3 month 3,000 miles bumper to bumper warrantee on top of whatever is left the factory warrantee.