The mid 90's style trucks with the manual trans and 4x4 had the NV4500 which has an issue with losing 5th gear. There is a fix for it but it is something to be aware of. 2wd doesn't have the issue IIRC.

Having owned and/or driven each of a 1993 (first gen cummins ram), a 1997 generation and a 1999 generation, I can say each generation is an improvement in comfort and ride quality over the previous. The 1993 was fairly rough riding, noisy, vibrating interior, typical of your 1980's style construction. Great looking trucks, however the extended cabs had the sideways facing jumper seats instead of a rear bench. The 97 was quieter, smoother riding and more comfortable. Having the rear bench was a nice plus. I bought another 97 recently that I will be setting up as my tow rig. The 99 had my favorite cab as it had the flip open rear doors which are awesome and it had a much more modern looking dash. Otherwise it rode about the same, maybe a little better. It also had the 24 valve computer injected engine which makes a little more power and definitely easier to modify. Howver the 12 valve engine had the simplicity and a little better mpg. The 03+ generation trucks with the common rail engine leaps and bounds quieter and more refined but I don't like them.