As far as Simms making the HOF, that's easy, where did he play? Both Luksa and Gossage, the HOF committee members from this market, have said there is definitely a Northeast voters prejudice against Dallas players.
Back in the day, they coined the word "finesse" to describe Dallas as a white collar team, rather have pretty plays than play hardball, even after that Ice Bowl, that grew even larger. A lot of that had to do with being the whitest collar market in the league and the rest was Landry's demeanor as a businessman and his love of the computer applied to football.
The fact that Chick Noll was an oenophile and had a collection of over 2K bottles of wine in his cellar at a time when jug wine ruled in the US was lost because he was in Pittsburgh, the poster city for blue collar.
Romo will have an uphill climb to get in the HOF and there was far too much polarization about him when he played. He got blamed for more losses than any other QB in the game while they'd make excuses for Elway, Kelly, Manning and Marino, Romo was the reason they lost. The only question is this new found media star image, will that help him? Sure as hell didn't hurt Simms.