I don't think the Jays need to be bottom feeders for 3-4 years straight though to draft at the top of the pile.
Trading guys like Happ, Estrada, Liriano, Donaldson, Bautista, Tulo (assuming those last 2 waive their no trades) plus pen arms (and I include Osuna)... should, in theory net more than just prospects. Maybe 2-3 roster players. Plus a few high prospects and they'd already be a few years ahead of drafting and waiting for 3+ years for them to start trickling in.
If done right and the guys they get in trade don't all suck, a few strategic signings and the Jays could starting the upswing by 2019, just in time for Vlad Jr to arrive, rather than maybe 2021 or 2022.