All good/great points.....just keep in mind that the "reality" is dynamic and Toronto can go from biggish market to mediocre market really quickly.
And vice versa. It's going to happen at some point in the near future barring an absolute miracle, given our team age and dearth of minor league talent. The key, IMO, is to minimize the amount of time that we're down again. If we ladle on a bunch more long-term salary, we're in a massive bind when the team hits the wall; Rogers won't want to spend contention-level money on a non-contending team, but we'll be sitting on difficult-to-move contracts attached to fading stars. Unlike the Yankees, who have been able to idle a shade above .500 and well above $200m while slowly turning the roster over and adding youth, we might have to make decisions that could extend our time at the bottom...cutting development and scouting resources, moving younger players as they approach free agency rather than making a push during their arb years to extend them out of fear that we'll end up with another Ricky Romero situation, etc. Or conversely, making short-sighted moves in the hopes of elevating team performance back to profitable levels at the cost of long-term aims. Those are the things that ultimately end up perpetuating mediocrity.
Luckily, tanking isn't really necessary in baseball; extremely high draft picks help, but it's in no small part a numbers game when it comes to prospects, and the trade market in baseball is much more profitable than in the NBA, because there's such a deep minor league system and large major league roster. We can trade off players in July and start (within reason) adding again in December; hell, the Yankees acquired one of the better prospects in baseball for the final few months of Chapman's deal, and then re-signed Chapman. Use the money saved to lock down some of the younger players long-term, as Cleveland did a few years ago. You just can't go free agent ex machina anymore; the costs are too high, and the returns diminish too quickly.