I am thinking the real "Red Sox Great Depression" peaked somewhere between 1918 and 2004. We now have actual expectations and a track record. This is fairly new in Red Sox history. I got into the team as a child around 1995-96, I had a sweet poster of Mo Vaughn and Jose Canseco looking jacked.
There was a real turning point in 2010. If we recall, there was a 2 week stretch where half of the starting line up and pitching staff got injured and really derailed the season. The team was OK that year, but the injuries were too tough to overcome. There was a sense that the team would make a big splash in 2011 - which they did. We all know what happened, but this kicked off a decade of break-neck failures and successes in rapid fashion:
2011 - Epstein Era. Greatest Team Ever fails to make playoffs
2012 - Tito canned and smeared on his way out of town. Bobby V. Punto Trade
2013 - Ben Cherington Era. Surprise Championship with the "core" intact (Pedey, Papi, Lester, Ellsbury) laced with good veteran signings
2014 - Terrible. Bogaerts first full season
2015 - Also bad. Bogie, JBJ, Mookie knocking on the door
2016 - Dombrowski era. David Price and Craig Kimbrel acquired. Playoffs
2017 - Still improving. Sale trade happens. Farm system takes a big step back after multiple trades. Playoffs
2018 - World Series and a great team wire-to-wire
2019 - Cracks starting to show, team gets off to bad start and is unable to turn it around
2020 - COVID year. Betts traded. Start of Bloom Era
2021 - Good team, shrewd FA signings, gets to ALCS. Playoffs
2022 - Bad team, Xander on the way out, juggling payroll in order to stay under luxury tax
2023 - Team looks, well, average. Lots of flexibility after the season, farm system ticking back up
All of this is to say, the last decade has seen 3 administrations. In that time, there have been changes to the draft and new technologies for player development. The way to build a championship team has changed, and the Red Sox are living through the growing pains of that. 2020 was truly starting from scratch in my opinion. Its been a grind for the last few seasons, no doubt. They are building the plane as they are flying it.
Frankly the bad times make the good times even better. I like following the farm system and watching the journey.