After 2020, we will be facing serious decisions. Not only may we be facing our 4th straight season over the luxury tax and maybe 2 or 3 years over the max line. That's 2 years, not 3. One could argue we may look to reset the tax after 2019, but I doubt we will.
As for "mortgaging the farm in 2004," are you claiming the Schilling trade (De la Rosa, Fossum and Lyons) compares to DD's multiple trades?
de la Rosa was 3rd ranked on soxprospects.com. Theo later traded HRam and A Sanchez for the 2007 ring (Beckett & Lowell), but that was after 2005.
The farm in 2004 had Lester & Youkilisto start the season, and also had HRam, Pedroia, Papelbon, A Sanchez, Shoppach, Brandon Moss, David Murphy & Manny Delcarmen. We were also able to add Ellsbury, Buchholz & Lowrie that summer, thanks to the generous comp pick rules that are no longer in place.
It's wishful thinking to expect anything like that anymore. It's very hard to build a farm when you keep winning and the rules have changed to make it very hard for winners and big spenders to acquire prospects through the draft or international signing systems.