I think if I were an Ayton fan, I'd actively like this trade. Or if he were paid less. But he's a guy who doesn't play in a way that successful NBA bigs play these days (perimeter shooting and good passing) and he makes a ton of money. Also, as others have pointed out, we probably could have made this deal without Dame involved at all... Phoenix was looking to dump him, and they did to us.
So it all comes down to what we can get for Holiday. Having him on the team is about as ridiculous as having Grant on the team, so I fear the Blazers might just ... keep him. Thinking we could compete for a playoff spot as our young guys mature and get experience. And the thing is that it makes more sense now, with Scoot added to Sharpe, than it did this time last year or (especially) two years ago (when we weren't committed to Grant and now Ayton on massive deals). So while I'd RATHER trade Holiday for future pieces rather than have a four guard rotation as we currently do, I think it's less crazy than it was in the past.
It's a "meh" deal for me at the moment. Happy to have Dame out of town and that we got something of note for him without teams shying away, and happy to see Miami fans disappointed. I won't root for Dame the same way I would have if we'd done a Toronto deal for Barnes (where it was a clear "win-win") but it's good we're moving forward.