My OOTP Mock is only done if we don't capture the World Series. If we were champions it wouldn't be prudent to make these changes.
If we do fail to win, I would start the offseason by surveying the managerial landscape and I feel like there may be a few options better than John Farrell. I'd lean towards Bryan Price because I believe the Sox are in need of a guy who can manage the Bullpen. I also feel like he might bring more leadership. Bryan Price has a solid chance to be on the market so I feel that's a fair singing to make.
After acquiring the manager, I'd shift the focus on obtaining a super star through a blockbuster trade by targeting Giancarlo Stanton in particular, who the Marlins are rumored to have interest trading. I'd offer Mookie Betts (Replacement player), Jason Groome (Top Prospect), Michael Chavis (3rd Best Prospect at his position on team, yet still top end) and Ben Taylor (An Extra Arm couldn't hurt) for Stanton at full money. I think that's enough young talent to get them to consider the deal especially since Betts is already pretty proven and costs substantially less. Boston doesn't have a huge need for any of those players right now as Stanton replaces Betts, Sale's in Groome's spot, plus we already have 3 left handed starters, Rafael Devers is better than Chavis at 3B and We have an abundance of RHP around Taylor's caliber.
For Free Agency I'd look into sniping a legit starter. The best team to steal a starting pitcher from for the Red Sox would be the Yankees. I'd go for Pineda hard at market value because he's a solid guy and he's on the right side of 30 years old. No older FA's are re-signed other than Nunez. Arbitration eligible players are kept. Maybe add a few cheap pickups.
With Pineda on board, I'd attempt to move David Price, as I feel he is cancerous to our locker room. He's not a leader, yet he's been placed in the role of one. We'd target the Dodgers, as they've taken contracts from us in the past and we'd hope they missed out in FA. We'd agree to eat 50% or slightly more of the money owed to David Price in return for Willie Calhoun, Mitchell White and D.J. Peters. Calhoun would then be groomed to replace Dustin Pedroia.
As for the Rookie Draft; First I'd put more resources into scouting because we have the money. As for players we'd likely be taking the BPA with our first few selections and then put the emphasis on filling in around them. There would be a priority placed on getting more Arms capable of becoming starting pitching.
I believe these moves will make the Red Sox a more serious Title contender in the short term and with the increased scouting budget we'd also cover sustainability at the top. Now it's time for the players to play the game!