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Doable, some plusses, (some minuses), but I've got some minor quibbles.
1) I just don't get this love affair with Scutaro.  At age 33, he has his first 100 OPS+ season.  Yes, he had a great 2009 season.  But he's 2 years OLDER than Jack Wilson.  He's coming off the best season of his career, while ALREADY heading into the "when does the decline hit" phase of his career.  This is like the poster boy for "sell high!"  You don't win by BUYING high.
Despite being two years younger, Jack has 3 MORE seasons with 140 games played than Scutaro.  Scoot also nearly doubled his walks in 2009.  The guy has a neon sign and rockets going off screaming CAREER YEAR!!! 
Okay, I get that he's been a bit more consistent than Jack W.  I understand the whole league transfer issue.  I could see an easy argument that he's EQUAL to Jack, (a tad better generically, until you add the age factor).  But, the real question here is -- Scutaro just had a career year, at age 33, at a very, very thin position.  He WILL be in a position to demand multiple years at high salary. 
Now, I'm not saying he would be a bad choice.  Plus defense, good bat for the position.  But, lest we forget, a big reason that Bavasi ended in the mess that he did was the horrid age mangement.  Is Scutaro in his age 34-37 seasons the SS that can bring a pennant?  Perhaps, but I'm not optimistic.  But, I'm certain he's in a much, much stronger bargaining position that Jack W. 
The reason I like a J.W. extension is because done well, it leaves open the door to upgrade, and move Jack W. to backup, (or more likely, move him on the open market).  I heavily suspect the size and length of any contract for Scutaro is going to make that much more difficult.  The key with Jack W. is to try and leverage the situation so you have the OPTION to go elsewhere if a stronger move presents itself for 2011 or 2012.  If my hunch is right, Scutaro and Jack W. are likely going to see their production lines converge in 2010. 
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Aside from that, the Hall/Josh Wilson situation is the one I hesitate with.  I'd prefer having the lefty Hannahan as a legit platoon option for Tui, (if he's struggling).  I actually don't like either Hall or Josh Wilson, as their K/BB number are so utterly bad, I cannot see either having much success for the rest of their careers.  The club needs offense, and one place you can leverage extra offense w/o sacrificing much on defense is to get good bats on the bench.  Neither Hall nor Wilson fit that bill.  I'm really hoping Z has something up his sleeve to move Hall as part of an upgrade plan.