Generally you are on the same wavelength that I have been on for some time. I would add that the time to make a decision on the direction for 2020 and beyond is the end of July. We will play both the Yankees and the Rays by then, The trading deadline will have passed and we will know if we have a realistic chance of making the POs and of any hope of making some noise after a WC game.
If after Aug 1st we decide we have to sell, I would bring some of our best prospects up to get a sustained look at them for either a low cost alternative next season or for trade bait.
My absolute keepers are Bogie, Devers and Vaz. My probable keepers are Beni, Holt, JDM if he doesn't opt out, Betts if he is willing to accept his true value in a contract, Marco, and Chavis. I listen to offers on any of those and particularly the ones making serious money. To me JBJ should be trade bait as he is likely to command serious money and his worth is questionable. Moreland is gone based on his inability to stay healthy, Pearce has nothing left, Nunez is gone as is Leon if we can get a replacement that can hit at all.
The pitching side is pretty open with more to be seen. We have Price and e-Rod havig good years, Sale under contract, Porcello is probably not worth what we would have to pay. Eovaldi is under contract and worth a look through the end of the season. Cashner is a FA but again we can look at him through the remainder of the season and offer him if he looks like a 4th or 5th starter. The BP need shoring up. We have some decent arms (not heads) in the pen like Barnes, Workman and Hembree. Do we keep Eovladi there or does he return to starting with time to prepare for the new season? I would look for several BP arms, including a closer.
My idea is to bring the team salary below the 1st level of the competitive balance tax by making strategic trades and trying to get some good young players who can come on in 2021.