It might be smart to leave Romo's deal alone if all you care about is pure profit. If you want to make your team better then you restructure Romo, TSmith and Witten and sign some good players in FA.
It is that simple.
While there's obvious risk with another large contract restructure given Tony Romo's age and injury history, his contract was designed to restructured last year and this year.
There was never any intent to have him count $27.773M this upcoming season, that's the largest current cap number in the entire NFL.
If Romo suffers a career ending injury in 2015, he can be released for cap savings in 2016 by using the June designation next year even with another large restructure. There would be an enormous amount of dead money in 2017, it could be $19M or more, but that would still represent a cap savings of $5M or more that season.
And the unadjusted cap will likely exceed $165M by that time, the Cowboys' adjusted cap could easily exceed $170M by then.
I'm not worried about potential future dead money with Romo's contract, it will be dealt with when the time comes.
It won't be the problem, not having Romo under center any longer will be the issue.
So restructure his deal again and focus on building the best possible roster while we still have a QB.
He (as a player, might become a coach in future) and Jason Witten (and Jerry) don't have many shots left at the target.