The Sox are currently 27-24 against teams that are .500 or better. I think if they can make the playoffs they have at least some chance of going deep. The pitching staff could be excellent with sale, bello and paxton leading the rotation and some of houck/whitlock/crawford shoring up the pen. The lineup is very streaky, but if they get hot in the playoffs I could absolutely imagine a scenario where the Sox are WS contenders.
I think there's a good chance they don't make the playoffs, and also a good chance that key players might not be healthy. But I see no reason to give up on the season entirely, and I don't buy that the team is guaranteed to flop if they do make the postseason.