I look for a lot of behind the scenes negotiation going on in the off season. I expect the Sox will try to extend one or more of XBo, Betts, and JBJ prior to arbitration - things we probably won't even hear about. I would also expect them to try to extend them until ~ age 30. Regardless of what happens in that effort the Sox will come out of those attempts with a better idea of what their financial obligations are going to be going forward. After that I would expect them to make decisions as to who's tradeable and who isn't.
That's why IMO the success of this team this season is so important. If these players can come out of this season with a good feeling about the team and the guys they're playing with they're more liable to tell Bora$$ to take a hike when he ( starts talking about holding out until free agency. They may very well see a good payday now and an even better one at 30 years old.
Edit: This is also why they shouldn't even consider trading Pedey - not that I think they will, but there are some who favor the idea. Pedey signed a team-friendly contract and the FO should demonstrate to these "kids" that signing with the Sox means that they'll be staying with the Sox.