Started with my 1st a NEW 1987 W250 Std Cab 8'bed, 360 auto 4x4, was a great truck at the time. Next was a Used 1995 Ram 1500 ext cab, short box, 5.9 auto 4x4.
Then decided to get a New 2005 Ram 1500 Quad Cab, short box, Hemi auto 4x4.
All were great trucks, being a 20 year ASE-Chrysler/Dodge Tech also helped.
Now retired I went back to a Second Generation 1998 Ram 1500 Ext Cab, short box 4x4. I prefer the slightly longer short box bed, with canopy I can stretch out.
I still have enough for passengers in rear seat when needed. Being a Tech during this generation helps too, because I have years of time on them.
I find the 2nd Generation easier and less expensive to mod and maintain.