Your post did get me to thinking about top 10 paid QBs, vs the next 20 paid QBs, or some variation of that. I'm more interested in yards per pass, percent completion, TDs, yards per game, total yards for each year, etc. You'd have to take the QBs over as wide of a sample size as possible, a minimum of 5 years, maybe the year before they hit the big money would have to be included.
It would be nice to answer the question if each guy was worth the money. If I was worth a crap today in stats, I'd figure out a way to run some ANOVAs to see if there was really any statistical validity behind, more money=better performance. Defining and calculating "better performance" is the open ended question.
I would not include Conf. championships or SB wins. They strike me as an unreasonable expectation. Maybe just up to winning their division and one playoff game.
I don't have the depth of knowledge that some other guys here have, but some thoughts off the top of my head are, Kirk Cousins wasn't worth the money (this year). Jim Kelly and Dan Marino were incredible but never won a SB. A few other QBs of lesser talent were on great defensive teams and won SBs, etc.