Lets say the boycott works well and revenue drops 8 million, do you think EM eats that loss? Do you think he will get scared and sell, or do you think he will simply replace Stone and *****e with 2 rookies and still be up a million?
I think it's fairly obvious what happens and it isnt what your selling. On top of that, EM will have the team listed as a seperate entity, so you might be able to damage the sens finances but your not bankrupting EM at all.
Now if you really drive the teams value into the dirt, the team will be moved to a city where its value is high and every single owner will be on board, they will not help fans in OTT drag down the perceived value of a NHL franchise, it would bring down the value of all the teams.
This also goes for sales, the list of people that will give EM 500 million for a team then spend another 400 on a rink is realistically no one. Its more likely another city with a rink ready to go buys the team, this way the NHL can save face and keep its crazy valuations intact. Also any potential buyer and Bettman know that if the team ever sucks again not only will the fans not show they will organize and try to bankrupt again, this makes moving the team a safer bet.
I would't be so sure your theory where someone spends 1 billion dollars on a bankrupt hockey team in ottawa makes the most sense.