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Great response, Doc.
In closing, let me just say that I think the time to go big is after you have shrunk the number of 'likely' negative WAR positions (meaning, likely to have somebody generating negative WAR for a decent portion of the season in a given lineup slot), to a small number - (3, perhaps).
At this instant, I look at Mariners 2012 and see:
CA - negative WAR likely for large chunk of season
1B - probably okay - but - negative WAR possible
2B - safe
3B - negative WAR likely for some portion of season
SS - pretty safe - negative WAR unlikely - (glove holds up bat)
LF - negative WAR for chunk very likely
CF - negative WAR for chunk extremely likely
RF - negative WAR for entire season possible
DH - possibly safe, but negative WAR possible
I only see one position (2B) that can be tagged as safe from a significant portion of the PT being negative with a second (SS) in the vicinity.  Part of the reason SS is questionable is that with Nick Franklin in the wings, the club may want to bring him up and he could potentially become Ryan's backup in the 2nd half.  As with all prospects, when Franklin arrives, the risk of negative WAR will be present.
With Figgins still on the roster, his money means he's still likely to get a fair amount of PT.  So, 3B takes a hit.
The OF situation is a nightmare.  I like Casper and hope that Guti bounces back, but mostly I view the entire OF as again becoming a revolving door of auditions.  If Ichiro gets more time at DH (to try and give him psuedo-rest), then that's more OF PT to cycle the prospects through.
The 2011 pattern suggest Jack can take the first half, look at what he's got and either call up new talent, or if it just isn't working, he'll trade for it.
But, ultimately, I view the middle infield as the only relatively safe bets for positive WAR for 2012.  I just don't agree with the idea that the big move is a good idea when you're looking at 7 positions likely to generate negative WAR for a significant portion of the season. 
Ideally, I'd want to feel comfortable with 6 positions before going long, (though I could settle for 5 if there's legitimate reason to be up on the specific prospects elsewhere).  But, I personally only feel comfortable at one position, and think there is little data to support being comfortable with more than 2.  I'm optimistic at several spots - but not comfortable.