It's funny how people are talking about the post 2016 Cubs as a failure...then talk about Jays 2015, 2016 as a success. Cubs didn't live up to dynasty expectations which were never realistic.
Long term free agent deals sell tickets...but they don't win you championships (very generalized statement and not 100% true but you get the point), yet every year fans complain about the lack of a big signing. George Springer can easily become similar to the deals which people are talking about for the Cubs. I really believe at maximum the Jays should look at 1 more long term deal free agent over the next 3 years. This off season is probably the time for it, and continuing to focus on reasonable extensions for the current lot.
As for a stocked farm, you can restock in a few short years (Seattle and Boston were 29th and 30th in 2018 and now firmly sit in the top 10 with Seattle at number 1), the key is to have some live arms in the high minors and a couple young (and potentially tradable) high ceiling bats throughout.
I don't know if this front office follows all my views, but I feel they have a good grip on what it takes to keep this team a 90 win team.