Fourth anniversary, fourth plan

Four years ago, the White Sox gave fans the greatest day in the history of their baseball-loving lives.
Therefore, it's only fitting that we take a look at a fourth plan of attack for the 2009-10 offseason.  This one comes all the way from Singapore courtesy of theghostofmansoolee, whose living entity served as the bullpen catcher for that 2005 team:
MUST-MAKE DECISIONS
1) Octavio Dotel: Arbitration, or not?
No arbitration. He's supposedly a Type A free agent, according to Cot's Baseball Contracts. But it's probably not worth the risk of having to pay more than what an aging reliever is worth in the current market.
2) Jermaine Dye: Mutual option, arbitration, or not?
Buy Dye out. Then you can try to see whether he'll come back for cheaper. I honestly don't know if there are any significantly better options in the FA market than him, and Dye sounds like he might come back for a lower price tag.
FLEXIBLE DECISIONS
3) One-year contract for John Danks? If not, what would you pay to extend him?
I think you try to lock him up for a long-term contract a la Gavin Floyd. you could do 4 years for $20 million that's backloaded, but then again I'm not sure how willing Danks would be to do that kind of a deal.
4) One-year contract for Bobby Jenks, extension or trade?
He's still a good closer, so you sign him to another year. But then I guess you try to deal him - he's going to cost too much sooner or later, and he could possibly be used as a centerpiece of a package to upgrade in other spots.
FREE AGENCY

5) Which positions are in most dire need of an upgrade?
I think you look at LF/RF and 2B/3B/SS - you can move Beckham to SS or 2B. It'd be good to get a left-handed batter with some pop, but those types of guys aren't exactly in abundant supply. There isn't an immediate contender for the DH spot, either, so that can also be utilized.
6) Name three (or more) free agents you’d consider, at a price.
Orlando Hudson for 2 year, $8 million-$12 million deal: He's solid defensively and can handle the bat. No qualms with Getz or Nix, but I think Hudson's still the better player. He's also a switch-hitter, which adds an element of versatility.

Chan Ho Park/Danys Baez/Guillermo Mota for 1 year, $2 million-$3 million/2 year, $4 million-$6 million: That's my order of preference. Dotel probably walks, so I think you need to try to supplant. I think Park might be the best; he was very effective out of the bullpen as a 7th-8th inning guy for Philadelphia.
Mark DeRosa for 1 year, $5 million-6 million: I think he'll get a lot of demand, but he can play a lot of different positions. He's in his mid 30s, though, so a longer contract doesn't make much sense. But I imagine someone will offer him a 3-year deal.
Jim Thome for 1 year, $3-5 million: I think he's got a couple more years of at least 20 home runs left inhim.
Bobby Abreu for 1 year, $6-8 million: He remains productive and patient. Something useful for any lineup.
Rocco Baldelli for 1 year, from MLC to $500K: Why not?
TRADES
7) Name three (or more) realistic trades that could improve the Sox team.
Bobby Jenks/Josh Fields/Chris Getz (or some combination of them) for upgrade at 2B, corner outfield positions or some bullpen help. You could also see if you can swing a deal to move Paul Konerko - this would conceivably open up a less taxing spot for Quentin and/or Tyler Flowers.
The one trade I can think of that would make sense is swinging a deal for Carl Crawford, though I have to admit that this would be a long shot.
The talk is that Rays will need to make a decision about whether they keep him or B.J. Upton. The Sox will need to come up with a decent package to get either (despite Upton's less-than-rousing performance), but the price tag will/should be steeper for Carl Crawford and will probably involve a guy/guys like Daniel Hudson and Jordan Danks. I think adding Jenks might help, because they have an unproven closer.
Crawford, though, would be a great player to feature on the lineup. And he's hitting his prime years. If the Sox really think they want to seriously contend, they should at least make an attempt to swing a deal for him. And as we have learned with past prospects, there's a reason why they are called prospects.
Of course, you'll need to give Crawford a hefty multiyear deal if you trade for him. But Konerko will be off the books after 2010, so that should free up some cash. I just might break into tears if this actually happens.
SUMMARY
To be honest, I don't think the Sox will spend much money in the FA market - they might bring back Thome and Kotsay, but that's about all I would expect. I think the Sox will probably make smaller deals to try to build around the starting staff and the likes of TCQ and Beckham. Peavy-Buerhle-Danks-Floyd is as good a rotation as any other and should keep this team in the contender category.
The question for the front office is how much more money the team's willing to take on; Crawford's 2010 option, for example, is $10 million, and he'd command much more if you tried to extend his contract. If you move a Jenks contract and a Konerko contract though, you get a little more flexibility - but then that would also introduces more question marks.
But assuming that I'm the GM and I can make all these moves, my preferences for signing would be Abreu, Hudson, Park and Thome, and I would throw my entire farm and Jenks topull of a deal for Crawford. For the 2010 payroll calculation, I'll use the highest I am willing to pay for these free agents:
Base: $68.65 million
+ Orlando Hudson at $6 million
+ Chan Ho Park at $3 million
+ Bobby Abreu at $8 million
+ Jim Thome at $5 million
+ Carl Crawford's $10 million club option for 2010
- Bobby Jenks' salary at $7 million (spitballing here on what he might get for a 1-year deal)
That takes the payroll to about $93.65 million, then you add on other arbitration figures, a backup catcher and a Mark Kotsay.
If you take the lowest number for all the FAs, then you're at $86.65 million.
It's hard to try to guess the salary figure, because I think the FA market may actually be even worse than 2009 (lag effect from the recession and still-uncertain outlook). So it may be that the Sox can be comfortably below the $100 million mark.
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A couple of AL Central notes:
*The Indians hired Manny Acta to replace Eric Wedge, which I think I'm OK with.  I'm going to miss Eric Wedge's uncanny ability to have his team ready to go by September, but Acta's coming off a 158-252 record and a lost clubhouse in Washington, so there may be hope for us just yet.
*Speaking of the Tribe, Let's Go Tribe had a detailed deconstruction of Mark Shapiro's resume in Cleveland that I meant to post a while ago.  Worth reading.
*Speaking of downtrodden franchises, Royals Review took Dayton Moore and Trey Hillman to task for stupid quotes. I also meant to post this a while ago. It's also worth reading.