If your interested in school, Humber College in Toronto offers one of the best jazz programs in North America. Take a look:
Jazz Performance – Introduction to Commercial Jazz - Humber College - Toronto, Ontario, Canada. I believe that program offers some kind of diploma which will then allow you to apply all the stuff you learned about jazz to music education and performance programs in a university. Make sure you've taken all the right courses! If you're not a Canadian citizen you will need to pay the international tuition fee. I think you'll be able to live in residence, but if not, there are some fairly inexpensive places to live. Parking comes at a premium here though! It can cost you up to $200 (usually on top of your rent) to rent a parking space in an apartment complex. It's cheaper to take transit.
Toronto and Montreal (which has some great music schools with jazz programs as well) are both great cities to perform in. There are always small clubs looking for people to play gigs on a weekly basis. And not just for jazz - there is all kinds of music going on here. Toronto hosts the North by Northeast festival every year, and then of course the Film Festival where a lot of musicians go to entertain the film goers. Montreal of course has the International Jazz Festival, which happens every summer and is comparable in size to jazz festivals in New Orleans.
That's all I can think of for now but I can try and answer questions if you have any.