Best older Dodge pickup for daily use?

This was my thinking for going older. Easy to work on, less stuff like expensive O2 sensors to replace.

I do like the idea of OD trans but '99 up will be cheaper than some old 80's Ram that was well taken care of? When I mean cheap, I'm saying like under $2k. I've seen some decent trucks in that price range (at least going by online photos and descriptions) and I figure any issues with a pickup from simpler times I can fix without too much expense.

I'm open to opinions on whether it's worth it or not on that budget too...