I think we pretty clearly have a "window" in 2017-19 where we have maximized our chances, after which we will face some uncertainty and the likelihood that our roster will look significantly different, but I don't really buy the subsequent "cliff" argument myself. This will still be an organization with a lot of money available to spend on improving the roster (particularly as contracts like Hanley, Pablo, etc. come off the books), and this year's draft and international class showed they should still be able to keep the pipeline of young talent flowing under the new rules. I think some people are making things a lot gloomier than they are in reality...the future is far from set in stone at this point, and if we're a bad team come 2020-21 it will be because we didn't play our cards right between now and then, not because it was somehow predestined.
(And as much of a prospect-hugger as I admit to being at times, having Moncada, Kopech, Espinoza, and the others we've traded wouldn't guarantee us a thing in terms of the future...)