Romo isn't going anywhere for a bag of chips. If we move him, it will be for premium compensation. If not he will be the starter when he returns, most likely. So having said that if he was trades this year, (probably only to Denver as that is one of the few teams it makes sense to trade for) or maybe the Jets (they won't make the super bowl this yerar with or without him, but Ryan may trade for him to fix the problem for next year) you would probably net three very late number 1's from denver or possibly two number ones from the Jets.
You would lose the security of Romo being here. Some of you are dismissive of this, but Dak's track record isn't long. You risk teams figuring him out and slowing his roll considerably, which is a substantial risk. It is easy if you say it really fast, but that doesn't change the fact it is a real factor. You are trading your starter. Let that sink in. Jerry takes a lot of risk in making that trade, so he isn't going to just give up Romo and be a laughingstock. He will get enough compensation to do the deal so that even if Prescott fails after the trade he can reasonably say, it was a trade that was worth the risk he took, and for most reasonable minds to agree with that statement.
Having said that, on the other side of the balance sheet it would mean cheap QB play for a couple of years. Not forever. I think Dak is on only a 3 year deak. We will get one more cheap year out of him and then he will cost as much or more than Romo does now. The cap savings matter, but not as much as the draft picks would.
With the three late round #1's you could probably get a late round defensive end to bolster the defense, or a replacement for Mo, if we don't want to pay Mo, which would save a ton of money, a linebacker to add to Lee and hopefully Jaylon. Or you could pay Mo (I would if I could get it reasonably done) draft that DE, draft a linebacker with our own #1 pick, and be in pretty good shape on the defense going forward.
Or for you trade Dez junkies, you could draft defense with the acquired #1 pick, and draft a receiver with our first round pick (or vice versa) and go young all the way with our new triplets and trade Dez for a #1. Rinse and repeat that process for two more years.
With the Jets, you are getting a top 10 pick this year, most likely. and a later round pick after that.