I think trying to stay highly competitive in 2020 would be a great mistake. It would likely prolong the return to greatness. It would have to include massive spending, because there is no other way to stay near the top next year. We have very few ML ready prospects that promise significant impact.
We need to identify which players will still be in top form by the year we set as the year of our return and get rid of the rest, even if it means paying significant parts of their contracts.
Assuming we try to compete in 2021:
Keepers:
Devers
Bogaerts
Betts (re-sign for 2021 & beyond)
ERod (FA in 2022)
Beni (FA in 2023)
Vazquez (Option for 2022)
Chavis
Hernandez
Travis, Dalbec, DHern, Lin, Walden, Taylor, Chatham, Duran, Ockimey
Possible re-sign, if the price is right:
Holt
Leon
May keep due to limited trade value, but look to trade 1, so we can reset the luxury tax for 2021:
Price
Sale
Eovaldi
JD Martinez
Pedroia
Look to trade:
Bradley (FA in 2021)
Workman (FA in 2021)
Barnes (FA in 2022)
Hembree (FA in 2022)
Wright (FA in 2021)
Brasier, Johnson, Velazquez, Brewer
Do not Re-sign:
Porcello
Moreland
Pearce
Cashner
1) Reset the tax in 2020 with the idea that we can spend large for 2021, if the outlook looks right.
2) Keep only players who will have positive value in 2021 or 2022 & beyond.
There is no easy way to rebuild the farm. Going over the tax lines every year and continuously having low draft picks and limited international pool money makes it nearly impossible, unless you have a sell off and/or a down year or two with a reset tax budget.