I agree most of us were excited with the work on July 1st, but ultimately this is where JJ needs to be smarter than us fans. He blew his load and prioritized the older player depth additions over the younger players firstly in trading McLeod to fit them in and secondly in leaving us susceptible to the offer sheets by bringing us too close to the cap with those moves.
His job was to foresee the team deficiencies and agressively go after them. Hindsight shows us that depth defense, goaltending depth and depth scoring are the weaknesses, but it wasn't too much of a stretch to think that a professional hockey mind would have seen these as the potential weaknesses.
Instead he focussed on keeping the older depth players we acquired over the past couple years (who weren't providing much depth scoring while on the wrong side of the age curve) and made all his additions to be smaller top 6 scoring options that wouldn't be useful down the lineup because of their size, when he had a top 6 forward with size bubbling under that could play down the lineup.
As such we actually ended up taking a slight step back in depth defense, standed pat on goaltending and generally treading water with depth scoring in that some of them are worse this year at scoring and some better but overall very similar and our top 6 isn't any better at all (maybe even worse).
Jackson failed and left Bowman in a position where he didn't have much flexibility to fix those errors.