Nice post. This is related to what fundamentally bothers me about Koby Altman. Koby has gone through/acquired 11 different players for the Cavs this year (Calderon, Green, Rose, Wade, IT, Crowder, Zizic, Nance, Clarkson, Hill, Hood). Some have been mild hits (Calderon, Green) others have been huge misses. But at least so far none of them have been big wins in terms of finding an underrated "diamond in the rough" who would pay off big in the playoffs, even though he had a huge trading chip with Kyrie. No Oladipos, also no one like Mirotic. If you look at the good playoff performers this year, many of them would probably have been available to us through trade -- Middleton, Mirotic, probably Donovan Mitchell (Utah would have made an unproven rookie available in a Kyrie trade...how would a trade of Jingles/Mitchell/Favors for Kyrie have looked now?), maybe Jrue Holiday, etc. There are other underrated players out there I'm sure.
As a talent evaluator Koby seems like he's at the level of an intelligent fan who checks out Basketball Reference stats and watches some NBA League Pass and is like, "hey that guy looks pretty good". I always sort of understand why he's doing what he's doing (although centering a Kyrie trade around IT was unforgiveably dumb, even I could tell he wouldn't be a good fit). But despite a lot of opportunity he has never shown that ability to find guys being underrated or overlooked by the rest of the league who had major potential as contributors. And everyone here seems to excuse him because he couldn't have predicted who would be good -- but that's exactly his job!
Anyway, he's doing a lot of learning on the job this year, hopefully he'll get better.