Seems like a perfect topic for the offseason, and I find your comment puzzling at best. It's extremely relevant because by acting a couple years in advance the Cowboys could lock those two Cowboys into place for 6-8 years.
Act early the front office has leverage. Act late and the front office has zero leverage.
I guarantee you the savvy GMs are giving this kind of issue tons of thought at this point with young players. Plan ahead. Think ahead. I guess I shouldn't be surprised that in a world where most people live paycheck to paycheck, such a discussion is viewed as premature.
You and me, and all the people who post here have no influence on what happens today with this team. Nor do we have any influence on what happens tomorrow, or three years from now. So while I applaud your looking ahead, the question about being able to afford both of those players will have other authorities that will cloud any decision today. And we have no clue about what those might be. Which is the real deal.
We have no clue.
So what a savvy GM might do, and what we seem to do here on this board have no link between them.
Discuss what you wish. But be advised there is no correct answer, because we don't know the circumstances the team will be in when those days arrive.
Just like someone said, Romo mostly likely will be gone by then. So keeping those two guys certainly seems possible. But again, there is so much that can happen between now and then, and some negative aspects to one, or the other, or both of the players, that this discussion is moot at this time.
But carry on. Reality has shown he purchases enough bandwidth for speculation galore.