DD's plan is probably better than mine. In his shoes the plan I'd put in front of Henry and company would basically say "We're going to have to go into the tank for 3 years in otder to clear the dead wood and cycle in some fresh talent. Here's how I'd prime the roster to make the team as competitive as possible in 2018, and here's why I think you can sell a rebuild to Red Sox fans."
I think our fanbase is more realistic than the FO gives us credit for, and we can be excited by just watching the kids play and mature. The storyline every year doesn't always have to be about the Red Sox are going to win it all this year. We Sox fans are in it for the long haul and not going anywhere, we will still come out for a bad year if we know that there's something worth watching if we do, such as the assembling of a young core that might take us to the top later on. For most of us that would be fine, just as long as we know what the plan is and it seems good to us.
Not sure Henry, an outsider, realizes this though, remember he came here from a Marlins organziation where the only way to draw fans was to win and that's part of his attitude in Boston, which I think is his mistake. We are not as quick to flock to the exits as he seems to believe.
And I think after the last 2 years of aging expensive players not helping the team you can easily sell a partial rebuild to the fanbase, particularly with some of the young guys like Eddy, Betts and Bogaerts showing their potential. If we didn't abandon the team in the last 2 years, a rebuild isn't going to change that -- in fact seeing the team communicate about, and then act according to, a plan to restack the team around that young core would probably be an improvement over the makd-it-up-as-we-go-along plan we seem to see laid out before us right now and may even improve fan response. We know our baseball here in New England, and a lot of us know the difference between shrewd moves that showed foresight and planning and reflex moves, and would respond better to a franchise that did more of the former and a whole lot less of the latter!
The only question is can you sell it to the front office, because it will mean a risk of reduced revenue (although not as much as they seem to be afraid of) and they haven't been prepared to accept that risk in the past. I personally suspect that both Theo and Cherington are no longer here because the front office will not accept the logical consequence the old core moving on and/or running out of steam, or of needing to reload and regroup for another run -- they want the harvest season all the time without spring planting and summer tending that sometimes has to go with it. New Englanders know better than that.