You said no undrafted QB has ever won a super bowl, and in response I said no defense as bad as ours has won one either.
And if you think 2-3 years/chances is enough for a QB to win a super bowl, then that's completely laughable. Even great QBs have more chances than 2-3 times, so why would you expect Romo to be able to get it done in that situation? Hell, look at Joe Flacco, he's just an average QB. But his defense continuously carried him to the playoffs, and he finally got on a hot streak and they won a super bowl.
Chances are, if we were to make the playoffs every year, Romo would've gotten hot one year and made a deep playoff run. All Romo needs is an average defense and coaching staff, but apparently that's too much to ask for.