Simons complicates the Blazers' backcourt situation (or requests a trade)
The two foundational pieces who have the highest potential of becoming All-Star-level players are Scoot Henderson and Shaedon Sharpe, although you could also make a case for Clingan.
It doesn't make sense that the rebuilding Blazers, who have gone off the record of saying they are building around Henderson and Sharpe, aren't starting both guards to give them the most opportunity to gain experience and develop.
If Anfernee Simons, Sharpe, and Henderson can't play simultaneously, Sharpe or Henderson's minutes could be more limited than what you'd like for an up-and-coming player who should have the keys to the franchise. It does help that Malcolm Brogdon is out of the picture, but keeping Simons around could still hinder Simons and Sharpe's development.
Another scenario the Blazers should be prepared for is if Simons becomes disgruntled. He's now entering his seventh season in the league and has gone on record saying he "wants the opportunity to win." It could be similar to how Lillard eventually requested out. The Blazers aren't even attempting to win many games as they look ahead to landing a top pick in the 2025 NBA Draft. They also have made it clear that they want to build around their two young guards, which could leave Simons questioning his long-term fit and role with the franchise.
The good news for the Blazers is that if one of these scenarios does come to fruition, Simons should have significant trade value around the league. Offensively, he's a highly lethal combo guard and could help a team that needs floor spacing and secondary playmaking, like the Orlando Magic.