At the risk of getting tossed out of here, I like the 2nd gen's looks the best, especially the 95 to 98. 5 non-quad cabs.
The 3rd gen and 24 valve 2nd gens are way too expensive to repair. I had a 3rd gen and it was nice, big brakes, loads of power, quick and always seemed to have something going wrong.
The first gens are nice, economical, have that brute look about them and I like being able to dive in and fix about anything that goes wrong.
I like the sound of the early 24 valve engines, then the 12 valves, and can you tell a 3rd gen is running without revving it up or looking at the tach? :-laf
I think my 1991 W350 rides better than my 2003 2500 4x4 did.
I guess when I weigh everything, I prefer them in the order they came out, 1st generation preferred to live with all around.
I love the way just a bump of the starter brings the early trucks to life. The 3rd gen truck had to be cranked until the crank sensor picked up the signal.
My 3rd gen had a lot of wind noise when there was a cross wind. I found that kind of disappointing. I also had a series of vibration issues in the front end, which they did finally get right. I had an Edge EZ on it and it actually would do as good or better on fuel than the 1st gens do. You really paid a penalty for anything over 65 though. It used a lot more fuel at 75 than either one of my first gens do.
I do miss the remote entry and a few of the other options, I will not miss them though when they quit and I have to either fix or pay to get them fixed.
As far as the plastic interiors, all three have loads of that!
I think as a group, they are the best looking trucks on the road. The only body style I really like better is the 67 to 72 GM pickups.
I am not sure the 3rd gen body is as good as the earlier two generations were. They definitely designed the third gens with a lot less fitting of body parts to be required. Time will tell. Glen
Attention: TDR Forum Junkies 
And the clatter, my god the noise! :-laf
