Ricky is right, with any FA (your own included), the following questions always apply:
1. How much are you willing to pay?
2. How much are you willing to gamble? (There are varying uncertainties with many players)
3. How confident are you that the player will be good (Woodson/Peppers/Pickett) versus bad (Bennett/Joe Johnson)?
Those are really scouting and personal-evaluation questions. You need smart guys in Gute+MM to make those decisions wisely.
It might seem that in past, TT was willing to pay and willing to gamble to resign guys we already had (Nick Perry, etc.); but he's been reluctant to gamble on outside guys. I think when it's a guy you've had, MM feels like he knows the effort and professionalism he'll get. Obviously with Bennett, they didn't....
With Wilkerson, Pettine should already know.
To some degree, I think the Packers have perhaps suffered a little by being so insular in both scouting and coaching. They don't have any scouts who have worked in any other systems, I don't think. They had Capers for forever, and usually promote internally within coaching.
I think we can see the advantage of bringing in Pettine from outside; he knows some other players and has some other personal connections. And perhaps some other ideas.
I kinda suspect that having more guys from other organizations gives more insight into personalities and players and coaches and coaching techniques etc.