One of my underlying things for Dillingham is his basketball history. He went to play for Kanye West's Donda Academy and then played for OverTime Elite (against the Thompson brothers, etc.). That's... not a great two environments for coaching. For OTE he essentially was a crowd-pleaser showing off his handles and jacking shots, like a circus performer.
What gives me optimism is that he came into Kentucky with that reputation and wound up fitting in very well into their offense. He was mostly perfect offensively, other than some freelancing and heat checks. Was practically their offensive engine to a good deal (+30% assist rate). He has a lot of seasoning to do, like knowing when to wait for screens and so on, but for his wild west background, he came a huge way.
On the other side, defense, he did things that I thought were amazing. I'd never seen such horrible judgment on rotations and positioning. Yet, he also did get better! Still awful, but he wasn't making the humongous, skin-crawling mistakes (like leaving a guy in the dunker spot to go back to his man). He seems mostly engaged on defense and seems to try.
Now, I do question the wisdom of going to Kanye West academy and OTE. The fact that he's a Klutch guy puts questions in my head. The fact that he's a bit of an influencer type. (He seems to like fashion.)
But I have reasons to think he can improve on defense. In large part, because his coaching seems to have been completely absent. Another part is that he seems to buy-in instead of just having no interest, like an Isaiah Collier type. The last part, he's very quick, can stay with guys, and doesn't get screened easily.
So... I shrug off a good bit of whether he can get better with seasoning and coaching. I've already seen it. Whether he's going to do it, that's another matter that interviews and background can tell a team.