To me the bottom line is whether you treat the fans fairly by trying to put a winning team on the field, and spending. I believe Henry has done both consistently.
The 2020 team might have been the first, and only, Red Sox team in the Henry era that obviously had no chance of making the playoffs going into the season.
I think a lot of Sox fans have been spoiled by success, just as it was predicted they would become once they broke through and won it all.