1. Industry practice these days - the contract will be a mild albatross in years 6-7. But if Pedroia can be a 3-6 win player for 4-5 years, it is a fair trade. He is a more valuable player than Ortiz, so treating him differently makes sense.
2. Cross that bridge when we get there. Pedroia's contract is pretty tradeable all things considered. You look at what Cano will get in free agency and this deal will become a screaming bargain. I mean, we locked up one of the more valuable players in baseball for the cost of a Ryan Dempster-level starting pitcher.
3. Ellsbury has had a wonderful season, and in 2011 he was one of the five best players in baseball. That said, his durability is a concern. But a bigger concern is that he will be 30 by September, and his bat is not valuable enough to say that he can maintain his value if he has to move to an outfield corner. I think a 4/5 year deal is possible still, but I think the Red Sox would be entirely justified in letting him walk and putting in Jackie Bradley full time.