Where do they improve when strapped with the Conley, Parsons, and Gasol contracts with an owner who refused to trade the latter? They aren't close to rock bottom yet, that could come in another couple years as Gasol ages but there isn't much hope of them hitting 30 wins during this 4-year window imo.
Exactly: the 4 years of badness are very correlated. In addition, they're in the west, where it's much, much harder to randomly make the playoffs with a shit team by adding a couple vets and trying hard.
My general impression reading these trade ideas is that a lot of fans penciled in a high Celtics 2018 pick, got super excited about the draft, and are now in the bargaining stage of grief.
Those are the absolute worst circumstances in which to make a trade.
2016 was a 2 player draft in which the Celtics drafted third, and were definitely totally screwed by not getting Jimmy Butler or Paul George. The Nets picks were going to convey in the 20s. Cleveland totally owned the Celtics in the Kyrie trade.
I'd argue that, given the tax and contract timelines, the Celtics, more than most other teams, should be trying to maximize variance in the future rather than minimizing it in the present.
EDIT: maximize variance wrt high-end draft picks, not overall team performance. And for lower draft picks, they'll probably be looking for solidish contributors.