Ha ha, this is the conundrum I find myself in when trying to decide what I want this team to do.
I've come to accept I'm totally ok with the team not trading Dame now, even if there is no shot to contend soon. Dame could increases his value if he comes back healthy, or the Blazers could get better ownership/management/etc to improve the decision makers.
But what I do want to see now is not have the Blazers screw up. I don't want to see the Blazers trade away youth, picks, or upside young players for non star veterans that add a small amount of wins. That would be even worse than the Roco/Nance trades. Basically if the Blazers trade their #7 pick (directly or indirectly) for Grant/OG/Julius Randle/John Collins, etc I would say it qualifies as that. The Blazers would be further down the path of not having a real chance to contend soon, nor rebuild soon. They would actually be completing moves that reduce the chance to actually add a star that could make a long term difference. Yes that chance at #7 is small. But its much higher than a chance at contending with average veterans such as Grant/OG/etc.