Brewers were mediocre to bad from 2013 to 2016. Their top picks from 2014 -2017 were Kodi Medeiros, Trent Clark, Corey Ray, and Keston Hiura. When they won 86 games in 2017 their best players were Jimmy Nelson, Chase Anderson, Travis Shaw, Domingo Santana, and Eric Thames. Later on, none of the their Burnes (111th in the draft), Peralta, Woodruff (326th) rotation that anchored the team were high picks. They've been successful because they make sound decisions at the MLB level and identify/develop pre-MLB talent well. Not because of the assets they collected over a lengthy rebuild.
All that to say, sustained success in Toronto isn't going to depend on making a bunch of top 5 picks over a 4-5 year period, or collecting a bunch of blue chip prospects. It's going to come from making consistently good decisions at the MLB level (Toronto does this) and doing a great job identifying and developing young talent (Toronto doesn't do this).
I have no idea what has to happen for Toronto to get better at developing talent. I have no idea if that's best accomplished via hires from the current President/GM or if someone has to come in from outside the org and change things wholesale from one of those big chairs.