1. Would the NHL put a team in Markham?
No

2. Would the Lefs be OK with it, and would it actually matter?
No, and of course it would.

3. Do you think Markham or Quebec could actually support a team with the Habs and Leafs so much a part of the culture?
Markham easily could. Quebec City does not have the economic base to support an NHL franchise.

If you could pick two cities to put expansion teams, where would they be?
Nowhere and nowhere. 32 is enough.
- Atomic Wedgie

If Alberta could up those equalization payments to Quebec, they might be able to support a team.

I know it's a rumour site but you should read up on things maybe just a little bit.

BCE is absolutely bleeding cash, with a payout ratio over 120%. They are selling assets to retire debt and pay their bills. They're more likely to cut their dividend in half than to go buying sports franchises.
Do you honestly think anyone would sell out of MLSE and then go take a flyer on a small market team in Quebec???

Not your finest hour...

they aren't expanding to Markham ever