MLSE is mostly concerned about being profitable. It is accountable to it's shareholders and must provide a strong return.
Their main point is remaining marketable. If they are in the media and people recognize their brand, they will generate revenue. Of the "big three" that MLSE owns, the Raptors are the ones that need to tread carefully. FC and the Leafs could lose year after year after year and they would continue to sell out games, because there are enough crazed fans to keep it going. The Raptors have a large following as well, but they have to be more careful with their product. Too many years out of a playoff race and season's tickets as well as what I call "brand sales" (merchandise, Raptors TV, etc) will start to suffer.
If any of these clubs could land a Steve Stamkos or John Tavares or John Wall or Darlington Nagbe, they absolutely would because they could market the hell out of them and generate themselves millions in additional revenues.