Those wing free agents might not be the best fit at this moment but the are probably the best talent we can add to the roster. ZaZa or Kaman arn't as valuable over a replacement level player. If there is an injury to one of Lillard/CJ/Wes/Batum, which I would say is unfortunately much more likely than not, then all of the sudden we have no depth again. Adding a wing also puts us in a better position to pull the trigger on a a trade.
Well said, Draco... you've got to weigh your free-agents in terms of short-term vs. long-term solutions. If a player that you're willing to spend money on is only a mediocre center that will only take you the the 8 seed, then why not invest in some better prospects on the wing instead? Are ya'll 100% sold on Barton? He had a nice run at the end of the season, but so have a hundred other middling scoring wings over the past decade that never panned out into anything.
Not to mention that you have to look at your depth chart in terms of how the players fit together and not just in terms of how many minutes are available. Lillard's a proven scorer and McCollum is as well (albeit not on the pro level, he'll still be a guy with the ball in his hands a lot). When guys like Lillard and McCollum have the ball in their hands and penetrate, force double coverage, etc., that leaves guys like J.J. Redick open to do what no one else does better - hit the open three.
I also know that Matthews is a good defender and a good shooter, but if Tony Allen is in your backcourt, that'll take so much pressure off guys like Lillard and McCollum that it'll make him expendable. He can guard the other team's best player at the 1-3 spots, and absolutely lock them down. Yeah, he's a burden offensively, but with a team that can actually score like Portland, he won't have to be called upon to score. Not to mention, offensively, he's still just as active as he is defensively. He's not the guy you want taking an open jumper, but he'll get you that offensive rebound and put-back that you thought was impossible to get.
Anyway, long story short, if you're not going to immediately contend, your free agency pick-ups should be considered for their long-term potential, and even if there's a "log-jam" on paper at certain positions, you've got to consider the roles the players will actually play for your team.