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Of course I'm thrilled with the Montero pickup.  It addresses one of the weak spots in the lineup cheaply (in terms of payroll), if Montero can play catcher.
It adds more upside rather than spending large on a player at his peak already.
Of course, as a prospect, there is always risk ... but there are few prospect bats out there with less chance of failure than Montero.
But, I would like to note that if Fielder had been signed, then getting Montero would never have even been considered.  Since Montero's ability to catch in the majors remains a question mark ... you CANNOT make that move unless you have the lineup flexibility to move him to DH if you are forced to.  Once you commit $25+ million to a DH you can't seriously consider any player "like" Montero, (big bat, questionable defense).
But, this is Jack working from HIS strength.  Since his arrival, the one constant is that Jack is good at wheeling and dealing in regards to prospects.  In regards to the FA market ... his record is spotty to bad.  The one multi-year FA deal was Figgins ... so not a lot to go on.
But Jack couldn't negotiate Branyan back into the fold.  He had to let him walk and then trade to get him back. 
Evidence (or lack thereof), suggests that Jack is not in the elite class when it comes to negotiating with PLAYERS.  Evidence suggests that he is excellent at dealing with GMs.  This is yet another reason that the club is likely going to be better off long term rebuilding from within.  If Jack really isn't good at player level negotiations, then better he start those negotiations with players who might already be prone to considering home town discounts. 
Z has a gift for judging young talent.  No, he's not 100% accurate.  But when the baseball world as a whole tends to hit .167 with prospect swings, Jack seems to bat closer to .400.  If that's your strength you need to maximize your swings with that talent. 
That said ... I like the idea of Fielder even less with Montero on board.  Adding Prince would destroy the flexiblity of making Montero a DH (if necessary).  The club STILL has too much uncertainty about future production to take $25 million a year gambles just yet.  A year from now, the club should have a much better take on whether it needs a 3B a 1B or a CF.