My thoughts about the season that just ended and how to proceed:
1) The Kimbrel trade was awful - Not because Kimbrel sucked, or because 5+ years of Madrigal and Heuer were the cost. I didn't feel that way on July 30, but the more I've thought about it the more I've come to believe that the Sox shouldn't have made any trades at the deadline. The MLB postseason is always a bit of a crapshoot. Even more so this year with everybody having played 60 games or fewer last year. Even more so for the Sox with two of the most valuable pitchers from the first half of the season, Rodon and Kopech, having a fairly good chance of wearing down, which is exactly what happened. Kimbrel could have been perfect this series and it wouldn't have changed the outcome. If the Sox had Bryant, or Schwarber, or Gallo, or Escobar instead of Kimbrel it still wouldn't have changed the fact that none of the starting pitchers lasted 3 innings. Sox should have just sat on the roster they had and lived with the results. If they don't think Madrigal is the guy they want at 2B, they still could have traded him in the offseason.
2) There is an organizational coaching problem - This goes beyond the drunk guy in charge, though he certainly didn't make anything better. This team is bad at: defensive positioning, holding runners on, swinging and missing too much, hitting too many grounders, and probably a couple other things I can't think of right now. There needs to be an overhaul in how this team uses data and applies it to how the players are coached.
3) There are too many similar hitters - Eloy Jimenez, Jose Abreu, Andrew Vaughn, and Jake Burger are all right-handed hitters who swing and miss too much, hit too many balls on the ground, and don't provide much defensive value. I don't think upgrading 2B and RF are going to be enough. I think there need to be some trades to diversify the roster. Trading Abreu or Eloy would be tremendously unpopular, and I'm not saying to do it no matter what, but if a really good return can be had, it needs to be seriously considered.
4) Catching is a problem - I'm a big advocate of Grandal's, and while he's proven his bat belongs in the lineup every day, he's just not working out behind the plate. This is a really tough problem to fix as there is a real scarcity of good alternatives. Nearly every available catcher is either bad with the bat, bad behind the plate, or both. Maybe the return on trading one of the guys listed above needs to be a catcher.