...and then there's a third position.
It is never acceptable for a team with the payroll of the Red Sox to finish last and it's the responsibility of the GM to see that it doesn't happen. I recognize that there are a lot of things - including luck - that go into winning the WS so frequent WSC championships aren't a realistic expectation but they should be respectable during their down years, using those years to to reload for a real pennant run.
I'm not interested in hearing "Wait 'til next year" year after year. I believe that when the FO sees that this may be THE YEAR they should pull out all the stops to win while retaining a core group of players that will make them respectable in coming years. They should identify those players and attempt to do what it takes to keep them. At this moment I see those players as Betts, Benintendi, possibly Bogaearts, and Sale. We're in the midst of a big run right now. I'm not advocating blowing the team up while retaining those four when this run is over but at the same time IMO everyone else should available for trade to one extent or another.
In short, look at your talent, decide when your best chances are, and make that run while you can. Then reload and give it another shot. But this business of having 25 years of "Wait til next year" smacks of the FO not being necessary to do what they need to in order to win as long as the fannies are in the seats that the money pipeline is flowing.