Cat:
Congratulations on the new ride. You're going to love it.
We had a Dakota many years ago. We alctually bought it the first (or maybe second) year they sold them. I belive it was around 1987 or 88. It was a great truck to drive in its day, although it had a rather gutless V-6 in it. My mom-in-law drove it most of the time, and put on a lot of very gentle miles.
When we moved down to the desert, we gave it to a contractor friend of ours, and he turned it over to his painting crew. Last I saw, it was looking pretty grim, although according to my friend it was still running great with over 200,000 miles on it.
After a year or so of being without a truck, we decided to buy a Tundra. We put 100,000 miles on it in just a couple years, so bought another Tunder (4WD this time), and put 100,000 miles on it---that only took us a little less than 3 years.
We still have the second Tundra, and except for the back bumper that I customized, it still looks like new.
Trucks are great.
Now we're putting most of our highway miles on in the Lexus, and it gets considerably better mileage than the truck or the Grand Cherokee.
Let's hope your son doesn't out grow the Yukon too soon. I don't know what you buy after that.