how do they get better? They have spent a ton of money over the years (on some pretty average players). They don't have cap room to sign a free agent.
Should they be happy with first round playoff exits (and an occasional 2nd round?). Between Lillard and McCollum they are making $52 million a year. Not much room to from there. They are constantly good so they don't generally get good draft picks. Do they just hope McCollum and Nurkic get better as they are still relatively young (24 and 27)?
I don't know. But if I was a Blazers fan I would be frustrated with their lack of being able to get better. Should you be happy with a team that is good enough to be a 3 thru 5 seed but never really a title contender?