My impressions, spread out over a bunch of these trucks 939series, 809series and M44series....total of maybe 50,000 miles.
Regarding ride smoothness, they vary. Every truck is different. I drove an M931A2 from Indianapolis to Waco TX by way of Columbus OH. I didn't notice it being any better or any worse than the standard cargo variant.
I drove an M934A1 long wheelbase with the expansible box from Las Vegas to Phoenix. I didn't notice it being any smoother than the typical cargo truck.
I'm certain wheelbase has an effect. I just don't think it's in the top 3 or 4 variables.
10,000lbs in the bed has a pronounced effect. Comparison of the same truck empty or loaded heavy is a big difference.
Pulling another truck behind you on towbars makes a little bit of a difference but not much - there's not much weight transfer.
Big squishy tires make a big difference. Going from g177s to 16.00s on the same truck makes a big difference.
809series trucks tend to ride rougher than 939series trucks, everything else being about equal.
The tamest smoothest army 5ton doesn't approach the ride quality of the roughest civvy 1ton. Silverstate55 has a really nice m931A2 with air ride seats. It rides very smooth, even though it's a short wheelbase truck tractor. Lindsey97 has a standard length cargo truck with 16.00's on it and the standard seats. It drives as smooth as any I've driven.
My M818, with 16.00's and HEMTT rims is about the harshest riding 5ton I've driven. Still, it's not the end of the world. I've driven it on several trips longer than 1000miles duration.