The Twins have three players who will be free agents after the season. Two of them play the outfield, Michael Cuddyer and Jason Kubel. The Twins have two outfield spots set, likely Span in center field and Revere in left. But competition for the third outfielder is wide open. The Twins have said they are going to try to sign at least one of the two. If they don't, its likely they will have to go outside the organization. The only real alternative on the roster is Rene Tosoni and he is a long shot at best.
Both Cuddyer and Kubel are going to be looking for multi-year contracts. Kubel probably has more value than Cuddyer. He is three years younger and a slightly better hitter. While his defense is not as good right now, its not unlikely it will be better than Cuddyer's three years from now.
Cuddyer has two things going for him with the Twins. One is that he is right handed and the Twins need right handed bats in the lineup. The other is that Cuddyer has been a clubhouse leader.
Because Cuddyer is older, it is also possible he will have to accept a shorter contract than Kubel. Kubel may be able to demand four years from some team, while Cuddyer may have to settle for two. With young outfield prospects like Hicks, Acia and Morales likely moving up to AA next year, the Twins will likely want to keep the number of years to a minimum.
Both Cuddyer and Kubel are type B free agents. That means other teams can sign them without giving up a draft choice, but the Twins will get a supplemental first round choice if they are offered arbitration and sign elsewhere. So if they decide to keep either one, in addition to the cost of signing them, the Twins will be giving up a supplemental first round draft choice. Its a bit ironic that designating a player a type B free agent actually results in a higher signing cost to the current team than to other teams.
My take is the Twins should go after Cuddyer as a priority. Its likely Kubel will see more offers early in any case and the decision of which may be taken out of their hands. With no real alternatives in right field, they need to keep one of these two.
With Mauer and Morneau possibly needing more time in the DH role, the need for full time DH diminishes. In fact, it opens an opportunity for Chris Parmelee if he is ready to take it. Still, if they could sign both Cuddyer and Kubel to two year contracts, or even better, get both to accept arbitration, that would be ideal. That isn't likely.