Its really the talent, assets, and how players develop that matter much more than the wins. I'm not as worried about wins this season and next season. Do the young players looks like solid long term starters? Do the Blazers have assets to add better players to the roster in future seasons? Is Billups the right coach once the team takes the step to trying to win all year?
This is really the first season the Blazers are putting an emphasis on winning. The west is brutal as well. I'm fine if they fall short of wins this year. But next season they need a more short term timeline that is realistic to be able to become a winner. For instance the Thunder won 22, 24, 40 games in 2020-2023. But that last team even with a losing roster was one of the most stacked young teams that were in a position to take a huge leap. Compare that to the the Bulls that also won the same 40 games that season but had little talent, few assets to improve.
Now will the Blazers be in a longer rebuild than the Thunder? Yes for sure, we are already well past how many losing season they had. But IMO that is because we tried this horrible "two timelines" fence straddling with vets like Grant/Ayton/Ant instead of 100% committing to an agressive rebuild. That is kind of a sunk cost at this point so changing Cronin with GM X won't really change that. I'm very interested to see what moves Cronin makes under Dundon. But I'm not going to judge the team primarily by wins the next two seasons.