City officials always bring up the insurance excuse. I think its a bunch of B.S. myself.
A good person to talk to about this and how to get insurance or get around it would be a guy by the name of Arnie Malcom.
He runs Luskville dragway in Quebec and has run a lot of airport drag races is some rural areas of Ontario. He does this every year so if anyone would know, it would be him.
Don't let him get involved too far though. He is more for bracket racing and is not a big fan of street cars. He should be able to point us in the right direction though.
I'll try to find his contact info.
If he can get some small town in the middle of north western Ontario to hold a race, then why not something right in the GTA?

ya shannonville has the show me the money tour every year from luskville. no reason why the GTA shouldn't be able to get something