I just look at it differently. Hahn has had a really bad record of using free agency to get productive mlb players at any price point, compared to other GMs. This was another offseason where he could show their scouting or decisionmaking has improved, even in looking for short term pieces or even using it to find undervalued assets.
It also lets the same team (front office) off the hook of the bigger picture.
We had 2 years of major league playing time available to find a power hitting first baseman. 2 years to find an innings eater that isn't great but can give you 180 ip and a 4.5 era. 2 years to find versatile, decent outfielders. These are roles you should be able to find through good scouting and playing time.
2 years with roster space where you can hunt for players through waivers, free agency, rule 5 drafts, trades and of course internal player development.
In that time they provided it to:
Dylan covey, Miguel Gonzalez, Hector Santiago, Manny Banuelos, Carson Fulmer, Wily Garcia, Daniel Palka, Nicky Delmonico, Avisail Garcia, Alec Hansen, Matt Skole, Casey Gillaspie, Ryan Cordell, Charlie Tilson, and Leury Garcia.
Of that group, the sox did not find any they were confident enough to give average production to, and needing to rely on free agency and trades to provide short-term, average production on the team because they could not do it through their own scouting and development.
In similar places, other teams have found at least decent albeit replaceable players. And while the sox have had a decent record of dumpster diving for relievers, they instead felt the need to pay market rate for 2 middle relievers after spending considerable capital to acquire lots of minor league and college relievers saying this was the new moneyball.
So basically, I think this offseason was indicative of a longstanding Hahn-era problem of not being able to squeeze greater value from marginal parts, and always feeling like he has to pay market rates for average production from multiple positions, to the point you end up with a higher team salary than you'd expect from the players on it.