I fly to Minsk quite frequently….you can go either Toronto or Montreal to Istanbul, overnight at one of the hotels in Arnavutkoy, then pick your Russian airliner to Mockva. If there’s nothing which I doubt, fly to Minsk on Belavia and from Minsk plenty of flights to Russian city’s.
No need for visa as being Canadian you’re good for 30 days in Belarus but I believe you have both Canadian and Russian passports (my son has both).
It’s about 1400$ to Istanbul and 650$ to Minsk and probably another 300$ to Mockva or St-Petersburg if you went this way.
Did you make time to stop in Romania to see your smoke-show GF that Subban hit on back in the day?