I agree with nearly all of your assessment.
I don't think we need Jackson to reclassify. I mean it's always good in theory to have more talent, but unless we go really short and play Wilcher and Jackson at the same time on the wings, that seems like it would produce a logjam at SG.
Unless one of them turns out not to be ready, somebody won't be happy. And it might force Dunn to consider transferring.
I wouldn't expect Trimble to transfer if Cadeau reclassifies, but it's a possibility. I'm assuming RJ returns but Caleb doesn't. If Caleb returns and Cadeau reclassifies, Trimble might feel the need to look elsewhere.
As for SF, we might be OK there, because Puff/Styles/Nickel could improve enough over the summer. But I think Hubert needs to look for someone in the portal, because we can't be sure of them.
We definitely need somebody up front, wheter or not Armando returns. If he doesn't return, Hubert should look for 2. We simply don't know whether Washington will be good enough next year. I'm guessing he will, but it's the same as the SF situation: we just can't know and shouldn't let the portal pass us by.