I'm not a believer in the win it all or rebuild each year theory of team building. Only one team gets the rings each year and there's never a straight path towards being that team. In theory, the Blazers should have been in contention right now if the Roy/Oden/Aldridge threesome had panned out. Injuries derailed that plan. OKC should have won a title by now with Durant, Westbrook & Harden, but the CBA and budgeting got in the way of that. Miami capitalized on a plan by 3 major stars to play together simply by happening to be able to have cap space to be able to pull it off. Boston did the same thing several years before that. That kind of thing rolls around every so often and I can't help but think that Olshey has an eye on positioning the Blazers to be able to do something similar after next season because he's sure keeping his contracts lined up so that he can maneuver then if he wants.
I say buying in to this draft, if it can be done for cash and filler, is a smart thing to do, but I wouldn't disrupt the core at this point. Add a couple of seasoned vets to the bench, get home court for at least the first round next year, and see how things pan out. If there's a need to do something dramatic, the following summer will be the time to try to pull it off.