We are not going to get any worthwhile free agent for a while. Most of the interesting ones will be getting $20M+ contracts in the near future and would pick other teams ahead of Portland anyway, like this year. Also, all our core players and potential players are signed up for the next 3-4 seasons which means we won't be in position to have to resign them and go over the cap. Yes, we will likely have to drop one of our high earners next year to stay below cap with CJ's extension (I think) but it won't be that difficult. It might happen with Ezeli that we don't have the funds to sign him but it is still two years from now.
The way I see it Olshey realized we have no chance to sign top tier free agents for a while and even mid tier FAs were going for north of $15M last year so the decision was to develop from within and see where it takes us. We may have been a little careless with that Turner deal but that's about it. With Leonard and Crabbe we believed in their potential, and in Crabbe we have a player who will still have good value if we decide to move him. Leonard could come back to bite us but IMO in current climate someone would take his $10M deal.
Harkless was a very good deal. Ezeli will prove to be a good signing. I don't see what else could have been done.
We will probably move Crabbe for Noel or Okafor in a couple of months, or put together a huge package for Cousins and everyone will be content again. There is no way we finish the season with this group, IMO we will get at least two new faces in and that has been the plan all along. Whatever happens until January is just bumping value of our assets.