To me it is too early to rate most moves individually but collectively this has not been a success. This management team has had 3 TDLs, 3 drafts, 3 FA periods to build a better team. That's plenty of time to change the culture, they communicated on it but never made a big cleaning they should have done. As a matter of comparison Bill Zito arrived at the head of FLA in 2020 he traded for Montour, Reinhart, Bennett in his first year, all in their D+7 that's one year older than the great core of CC Dach Newhook as a matter of comparison.
I liked the idea of reclamation projects in Dach / Newhook to speed up the rebuild who are two players that I really liked at draft time. At the time it was clear Dach had vision and hockey IQ and he could be great if he improves his shot, well he did not in 6 years in the NHL. Right now it does not seem they won that trade.
Trading Toffoli rather than Anderson at the time seemed like a mistake to me and I'll maintain it was, because Hughes is now stuck with that contract. I won't blame him for the Lehkonen trade, he got a 1st and a 2nd, let s see how they develop.
To me it s rather about the moves he did not make than the moves he made, even though I think hiring a non experienced coach to coach a young team is very risky because you risk developping bad habits.