1) What exactly did Jerry Jones do to lose the last games vs the Giants and skins these past two years?
As GM, he fielded a team with enough talent to get to a win-and-in situation. The rest is up to the coaches and players.
2) If resigning Romo was a bad decision, what was he supposed to do as GM? Get Tebow? Vince Young? Carson Palmer? Pat White? Rex Grossman? Matt Hasselback? Roll with Orton? draft geno Smith? I don't recall a lot of options and don't recall seeing any real good options at that time. Did he overpay for Romo? Yeah. Although, some of that is greed on Romo's part along with almost every other player in the NFL. If Romo truly wanted a ring over money, he would have taken less ($3M/year less would have been a nice gesture on Romo's part) so the team could have got some additional talent to help him. It's not like Romo needs the money. He has plenty and will make a lot more golfing when his football career is over.