I am going to put myself into Theo's shoes for a second...
Catcher
So, what are you gonna do at the catcher position. You have Salty, and you have a player in VMart who wants to come back pretty heavily. But it is pretty obvious that VMart's days of catching are coming to a close. Which is why I wouldnt consider VMart a C at all. But Salty is far from a guy who you hand the position to outright, since Salty might end up going the way of VMart and moving off the position due to his defensive deficiencies.
So I would follow the big rumors that have flowed through this site recently and I would go out and get Chris Iannetta. He is going to cost a pretty penny. But he's a local kid with power in his bat, a good plate approach and a much better catcher than either VMart or Salty. He would probably cost you Doubront + a few other close to MLB ready guys, but he would be worth it in Fenway especially.
First base-
So, you have Youkilis and Beltre at the corner IF positions this season. Well, Beltre is a guy I wouldnt touch with a 10 foot pole on a long term deal and my guess is that he rides his way out of time with Boras pulling at the reigns. And the 3B market is ABSYMAL after this season aside from Beltre. So, the most logical thing to do is move Youk back to 3b. Then, you have a lot to choose from on the 1b side. Here are the list of guys who could actually make sense at the 1b position
VMart, Dunn, Konerko, Lee, Pena
Those are 5 guys with solid above average to elite bats. But you also dont want to run into a player who is going to have to be moved off the position into a DH role if you give them a long term deal. And with Fenway being a righty hitters dream, it might make more sense to go out and get a righty. Also, with AdGon probably not being available until the deadline in 2011 at the earliest, the sox are probably not going to want a 1b that is locked in long term. So, how about a 1 yr deal for a guy like Derrek Lee? He's having a massively bad yr, but was playing on a team that sucked monkey ass this yr in Chicago. If he shows any signs of life in Atlanta, how about putting him at 1b and seeing if he can find his stuff from 2009, where he batted .306 and hit 35 homers. He's very good defensively and should be completely healthy. And if he bombs out, it's a short term deal and allows you to chase Adrian Gonzalez unimpeded.
Left Field
I think the sox are going to make a major move in the OF, since Cameron and Ellsbury obviously havent worked out this season. I do expect the sox to move Ellsbury back to CF and use Cameron in a 4th OFer/intermittent DH role. But the sox need some more thunder out of their LF position, especially with Drew showing some signs of regression. You could go out and get Brad Hawpe and hope that this yr is a fluke? Hell, I'd love for him to be on the Yankees. But I think the sox are gonna have money to burn and going that route isnt as guaranteed as it would be if you went out and signed Jayson Werth. Give him a 4 yr deal a la Jason Bay and watch him club homers onto Landsdowne street on a nightly basis. He would be a beast in Fenway. This then allows redundancy in CF with Cameron and allows the sox to use Cameron/Lowrie/Salty/Iannetta/etc at DH if needed....
Designated Hitter
I am unsure of what to do about Ortiz. The 1 yr deal is absolutely enticing, and there is no buyout, so it is truly a $12.5 million option. But what would his worth be? Maybe $8 million? So, is it worth risking $4.5 million by just picking it up, or do you risk losing him over that same $4.5 million if another team came swooping in and signed him to a 2 yr deal? One thing I would absolutely not do is sign him to anything more than a 1 yr guaranteed deal. I'd add club options on, but no player or vesting options. He's a ticking time bomb and flexibility is important. I think I would just take the option, pay him the $12.5 million and at least fill the hole for 1 more yr until guys like Salty and Iannetta settle in or until the sox see what their 1b situation looks like.
So, the lineup that I put together goes something like this
C- Iannetta/Saltalamacchia
1B- Lee
2B- Pedroia
SS- Scutaro/Lowrie
3B- Youkilis
LF- Werth
CF- Ellsbury/Cameron
RF- Drew
DH- Ortiz
That might do the trick while also keeping two major offensive positions (1b/DH) very flexibile