Not only those players, the Blazers would probably have Duren instead of Grant, and at least some young talent from the Clippers trade instead of nothing. Maybe the Blazers would also have a few more young pieces or picks instead of Hart from the CJ trade too.
The time to setup the next decade of the Blazers future was when the team fired Olshey. They didn't have to rush into the revamp; instead they could've first spent time to get a great GM and empowering him to do the best long term decisions. We got the shit moves this team has done starting in February; after that started even a great GM wouldn't have been able to save this mess.
The only redeeming chance could be if Sharpe becomes a superstar. Unfortunately he lasted 5 minutes in his first game. Would be great if he can become the superstar and the Blazers contend with him and Lillard; it just seems like such an unlikely long shot gamble; feels like this franchise threw everything on one number of the craps table. I guess it could work, and I sure hope it does, but that doesn't seem at all like good long term planning.
Compare this mess to the other franchises such as the Thunder, Pelicans, Jazz, etc who have long term assets or other teams that have great current players. The Blazers have a poor collection of both; as evident by only the Wizards and Kings in the entire NBA being ranked worse in ESPN future rankings.