The concern isn't whether they are winning are losing over the last two months, or what they did or didn't do in 2005 or 1977. Also, beating a tanking Cleveland team is not even a minimal threshold during a "multi-championship window".
The concern is whether this team will be healthy enough and playing in mid-season/strong form heading into October to be a legitimate WS contender.
The legitimate concerns are:
Rodon's shoulder is a concern, as is his innings count vs. previous innings counts the past few seasons. Is he out of gas?
Lynn's knee has been bothering him for at least a month, and has won once since his July contract extension.
Kopech has been very inconsistent since returning from the IL, and has regressed in terms of stretching out. Will he be able to contribute in October?
Grandal has caught 6 Sox games in the past two months, can he catch at least 2 of 3 / back to back games in October, and if so will it impact his hitting or the defense he attempts beyond framing?
Is Engel done, leaving defensive hacks Goodwin/Sheets as very possible RF possibilities vs. RHP in the playoffs?
Does Tony have enough strength this late in the season, or can someone on the bench be assigned to assist raising Tony's hand in the air with four fingers raised to signal an intentional walk to umpires when circumstances dictate, or will he need a few more lessons before grasping this "new rule" in 2021 or 2022, and continue to blame catchers or missed pitches in the interim?
Lucas and Tim are also out, but based on progress reports they are at the lower end of potential concerns at this point, and will hopefully be themselves in 1-2 weeks.