I didn’t really like the whole “Cliff and Pam magically become as wealthy as the Ewings via a long-lost, presumed-dead mother” angle, even if it led to great storylines.
A key factor in the Barnes-Ewing field was that it pitted the haves against the have-nots, and just changing it almost overnight, in something of a retcon-adjacent way, changed its nature...
Now instead of remaining a shrewd, scrappy, up-and-coming rival gunning for the big leagues, Cliff had to become a buffoonish idiot to remain a have-not. I’d like to have seen him develop some wealth in a different way, perhaps getting into the oil business via his OLM status. That would have been a high-profile position that would have opened some doors for him in a few different industries when he left the public sector.
It wouldn’t have been far-fetched for him to get there as a lawyer - a new generation Harv Smithfield or something. Imagine if he took on Ben Maxwell and some of his cronies as clients and built up a private practice around that.
I’m guessing a big factor in Cliff evolving into the “perennial loser” in his feud with JR was simply that Kercheval wasn’t tall and classically handsome like the Ewing brothers, and was also a fantastic comedic actor with a ton of range.
For all the “Cliff is a loser” talk, he sure ended up better off at the end of the series than the beginning, as opposed to JR, who in many ways was the real loser, even halfway through the series.