Greg Oden's main offensive move is being a receiver in the pick and roll. On occasion though he does get deep in the paint and Portland has had difficulty getting Oden the ball in a timely fashion. Hedo enhances Oden's offense. Why? Because Hedo is a good midrange shooter it pressures defenses when he handles the ball and this makes it easier for Hedo to loft a pass to Oden; second, Hedo's height allows him to see over most small forwards increasing the chances that Oden can get the ball when he needs it: when Oden is right under the basket.
In addition, Hedo's ability to execute the pick and roll would have created better matchups for Roy (no small forward guarding him).
Hedo's decline of the Blazer's bid for his talents highlights what the Blazer coaches and management see as a weakness in the Blazer's skill set: the ability to operate the pick and roll. Roy is fine but teams will (did) use taller small forwards to defend the pick and roll making it difficult to execute the play successfully, and increasing the wear and tear on Roy by having to do all of the playmaking.
So it seems the Blazer's management doesn't think that Outlaw or Batum can effectively run the pick and roll. Why else acquire Hedo?
Win now? This is not a realistic goal. Remember, while the 76-77 blazers were the youngest team ever to win the championship, that team had experience from top to bottom from good to great collegiate programs. The Blazers have guys who are still years away from having that kind of experience (basketball and otherwise). So acquiring Hedo to win now was not the goal of the trailbalzers.
Did Portland want to see if salary could overcome geography? I think they got their answer: not in Hedo's case. Will Oden, Aldridge eventually bolt to other locations when their contracts are up? In spite of monetary rewards for staying in Portland.
Will McMillan stay if Portland has difficulty in getting veteran talent? McMillan was apparently sold on Hedo's abilities (perhaps that's why Portland management sent him to talk to Hedo in Orlando) and McMillan has complained of a lack of veterans on the Blazer's.
I think Blazer management just got some valuable experience in regards to building a playoff, and championship, team, a team that makes it out of the first round on a regular basis. Clearly rebuilding has been a success for Blazer management, now they have to learn how to manage a successful, winning, team. That appears to be tougher to learn than rebuilding a playoff qualifying team.