I used to think he would have a better career in a WCO, but now I'm not so sure. His best attribute is the intermediate throws and while I wouldn't call him the most accurate deep ball thrower in terms of placement, he's more or less very effective on deep throws. His worst skill is the short passes.
As far as being healthier, his injuries have come from things like his hand hitting a linemen's helmet, a missed block by a rookie fullback, miscommunication in trying to get the Eagles who were out of position, etc.
What would have helped his career, IMO, is a more experienced HC and O-Coordinator that understood his limitations and his strengths. I think Romo is a bit like Roethlisberger...he works best with a quality run game and commitment to the run. When he starts throwing too many passes, that means he's throwing shorter passes to try and keep the ball moving and it's not his strength. And without a run game and a commitment to the run, his beautiful play action doesn't fool anybody. And I'll say it again...the metrics show he starts to get worse right around his 36th attempt. Obviously, you can't always prevent how many pass attempts we make, but there were plenty of games from 2007-2013 where he threw the ball way too much for no good reason and it didn't play to his strengths.
As far as health goes, he had a relatively healthy career. It's just that he's up there in age and Jerry actually thinks that because he didn't get playing time his first 3 years, that it will carry over to present day. But, the body doesn't work that way.
YR