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Bad luck?  Not really.  Except for Guti, the 'general' results are completely and totally predictable.  If you repeatedly opt to pay "current" value for players over 30, you will be repeatedly paying much more than their production value in future years. 
Injuries happen, of course.  And every team must deal with them.  You're always going to have some DL guys who are not producing.  But, an Aardsma going down is what allows you to get a look at a Lueke or Wilhelmsmen ... perhaps earlier than you planned.  But, that's just normal baseball management.
Guti is the one guy who went down from a random, unknown and unpredictable cause with no information or expectation of future performance.  In that one instance the club was unlucky.
Signing a future HoFer to a contract on an age 34-38 contract "expecting" 4.2 WAR per year for the term assumes discount early and overpay late.  And anyone who isn't making that assumption is an idiot, because there is 100 years of baseball history that says it is going to happen.  It's NOT bad luck.
But, even the Wilson contract can be traced back to Bavasi.  The instant the club locked in on Yuni/Lopez as the middle infield of the future, they made an organizational decision to trade away any future options for the MI. 
Getting rid of Yuni was Jack's choice.  But Wilson was a "best we can do under the circumstance" selection, who like every other 30+ veteran was an asset in decline from day one. 
The simple reality is for every $4 million you spend, you "expect" 1 WAR, hope for 2 WAR and accept that 0 WAR is a possibility.  When you buy guys over 30, you expect to get most of your value out "early".  You're "intending" to pay the piper for the decline in production "next year".  (And you hope that salary inflation takes 'some' of the bite out of that hit).
For almost 5 years, the club attempted to 'move forward' with Yuni and Lopez being the only hitter prospects in play, repeatedly buying 30+ veterans and trading away prospects. 
Today, the club has two young hitter prospects in play.  They are BOTH of better quality than Yuni/Lopez.  But, if your "plan for success" consists of assembling 3/4 of a roster in decline, (unless you're spending $200 million), then sucking isn't bad luck.  It's being bad BY DESIGN.
What kills me is that 2011 should be pointing out the *HUGE* advantage in prospects versus veterans.  There are a bunch of negative WAR values this year from sub-30 players:  Saunders (-0.7), Peguero (-0.7), Lueke (-0.7), Mike Wilson (-0.3).  But, the big difference is ... those guys are back in AAA and there are new guys up.  If you negative WAR is generated by "free" players - you *CAN* swap them out.  But, when you're paying $54 million for negative WAR, you can't. 
All that said.  Most of the age 30+ contracts currently on the team are still an artifact of the empty farm and bad management of the previous regime.  Even Figgins is here because when Beltre was ready to walk the only farm option was Tui ... and the club (correctly) assessed that Tui was not up to the task.
What's funny is that when Guti was named as the "centerpiece" of the Putz deal, MANY howled at the idiocy of the move.  Many also were (at best) skeptical of the Ryan acquisition.
Ryan has a 2.2 WAR for the season ... the top WAR of any hitter on the team.  Gee, he was acquired before age 30.  Go figure.
Kennedy is the ONLY "value" bat on the roster above age 30 ... and after a killer first half, is fading.  But, pluggin holes with 1-year FA deals for 30+ guys is absolutely necessary.  You'll pick some winners and some losers.  But, you'll retain flexibility for your farm to substitute a "free" productive bat the next season.
As it stands today, if Liddi turns into an MLB 3B in 2012, the club will be "effectively" paying him Figgins' salary to do that ... whereas, if some bat steps up to fill in as DH ... you're paying nothing for that production, because Cust is gone.