Still agree with Gary that the club have learned some lessons and this summer, while not the deus ex machina we may have hoped would return us to the top did, at least to me, represent a change in how we operated. I think all the players we were heavily linked to and the ones we bought fit a common thread (lulz British) in that they're all players who are making their first genuine step up to the top level, and are hungry to establish themselves.
None of them have inflated egos, nor have the attitude that they've already made it, and are simply here because it was the best move with the best wage packet they could manage. Additionally all of them fit quite comfortably into our wage structure without threatening to destroy it and have half the squad disgruntled and looking for a pay raise like we faced in the 1.5 years after the Alexis purchase with him turning into a pumpkin.
I also would say that while not getting in a replacement for Herrera, because we seemingly only had Longstaff as a target isn't great, I think it's meaningful that they didn't just buy for the sake of buying at the 11th hour in desperation. Sometimes not buying is a better option than reaching for a less preferred target. Klopp faced exactly this criticism when he wouldn't go after any lesser, secondary CB targets in summer 2017 after the initial VVD transfer debacle. He made do with what he had and when they had another opportunity to get in their preferred target they successfully pulled the trigger.
Should Longstaff be the sole preferred candidate for that position like VVD was for Liverpool? No, I don't think so, but this is symptomatic of our overreliance on managers to dictate transfer shortlists. I think Ole and his staff provided targets they were comfortable with, with the limited leg work they likely had a chance to do heading into the summer, and didn't budge. Ideally we would actually get in a DoF/technical director who would take into consideration the attributes of player the manager wants at certain positions as well as some options, add further targets to the list who also fit the bill according to our scouts (who based on the young talent we've identified seem to be better than we've been led to believe in the transfer market) and give Woodward a more in-depth list to work with.
That final piece is where I think Woodward still deserves plenty of criticism, because it has led to us getting fixated on targets and not being able to move on when quoted an unreasonable price. Instead we have to haggle over a fee for months.
Another consideration is that I do think when it comes to "replacing Lukaku" Ole genuinely decided he preferred to promote internally with players like Greenwood, Chong, Gomes, etc. at his disposal. It's a big gamble on his part, but given what the ST options available this summer, I think it's a roll of the dice worth taking than spending big on players like Sebastien Haller, Wasim Ben Yedder, etc. That is contingent on that money still being available to use at a later date if players come available that add to our squad, which I think is the case.
As things stand I think if we'd simply got in another CM so that we weren't inevitably going to have to lean on Garner to play a decent amount of minutes out of necessity and provide some more steel in midfield, we'd all be much closer to being on the same page regarding how this summer panned out than it did. That said, I do think there were promising signs about how we operated, but more work needs to be done to improve our process before January and next summer, namely hiring a technical director to work with Ole and Butt.