The tax comes at the end of the season and like you said the repeater ta is where you start getting hit hard. The Blazers will have trouble moving any of the Turner, Crabbe, or Leonard contracts for sure, but only this year. Next year they’ll have a much easier time moving them because they’ll all have one less year on their deal and they can do that before the tax hits them.
Basically I’m saying they will have an easier time running than you think. Also I think you haven’t accounted for how little Paul Allen cares about this fine even if they do get hit by a repeater tax. The man is richer than every owner (besides Steve Ballmer) put together and he loves his Blazers more than anything. The situation is not as grave for Portland as you made it sound.