I'd give Naps 4 yrs / 54M in a heartbeat (prob even more).
So, a 31 year old guy with a career OPS of .863 who had a huge decline from 2011 to 2012 is going to get a 4 year 54M offer from you to play 1st base, DH and backup catcher? Why not simply offer low farm scraps for VMart (who only had 2 and 26 left), or, if the Tigers want more, simply go one year and low single digits for Loney and platoon Loney and Gomez at 1st base until a better value and fit presents itself?
I think Napoli's value and fit ends at 10 to 13M and 2 years. I'll be suprised if anyone bids 4 years market rate, but examples like Crawford and Hunter are not valid reasons to pay market for someone like Napoli.
I agree on your trade suggesting for J. Upton, with the expection that I would approach a little differently. I would set aside the following pool, getting rid of Ellsbury's 10M cost for 2013 and using his draft compensation to reduce the loss of some of the current young talent:
Pool for J. Upton trade negotiation:
Ellsbury and his draft compensation (can be flipped to a third team)
Brentz (can be flipped to a a third team)
De La Rosa or Webster (can be flipped to a third team)
The DBacks pick of any one player on the farm except for Barnes and Bradley, Jr. (can be flipped to a 3rd team)
The rumor is that the DBacks are seeking a MLB ready SS, 3B and Pitcher. The above package would be able to be flipped to provide that. Both Brentz and Ellsbury and his draft compensation will provide at least 2 MLB starter ready SS and 3B. And in the event that the DBacks don't view De La Roasa or Webster as MLB ready, one of them and another upper tier prospect will net a 2nd tier MLB ready NL pitcher.
And in the event the DBacks provide offer sheets that show a clearly better deal, I would add Bogearts to the pool and subtract Brentz. I seriously doubt any better offers will be on the table. Using Ellsbury and his draft compensation is the key to the allue of the package and saves at least one year talent, over other offers.
It has no net affect on the 2013 labor costs, as Ellsbury's cost is swapped for J. Upton.
The bridge to Bradley is short and cheap. J. Upton and Bradley, Jr. stabilized what would be a terrific modern skillset OF for many years to come.
The pitching market is simply full of overpriced 2nd rate pitchers.
The best way for the Red Sox to get better, short and long term, is to acquire J. Upton to go with Middlebrooks and Ortiz in the middle of the order, and to go with whoever they finally replace AGon with as the long term lefty slugging talent.
The market is there to improve an offense that, when adjusted for lack of consistency and for the park and league factor, hasn't cut it since Manny left.
The current costs on Lester, Buch and Lackey need to produce. Chasing other 2nd rate pitchers is just a way to compound the problem. Doubrant should be retained, and Tazawa and Morales should be in the starting pitcher depth pool for 2013. Guthrie is the best 3rd rate pitcher option, with way better value than the 2nd rate pitchers. Guthrie's market value ends at 2 years and base 5 or 6. There are other low single digit/minor league veteran pitcher options that far exceed the value of the 2nd rate FA pitcher and pitcher trade market.
A team trading, or dumping into a FA, a starting pitcher is almost always a red flag for physical or mental health issues. The lone exception would be for teams with financial problems, and those should be scrtutinized because those teams know their better talent better than anyone else.