Fortunately, I don't need to work. I began working at 15 and I'm now 51 and I have some savings. I'm very much into the Arts and I think Montreal might be a good fit for me. I have been to Quebec and I'd like to know the difference between Montreal and Quebec when it comes to American's moving to a new Country.
Well in my post i referred to Quebec in general (the province)... but the only city really for you would be Montreal... Quebec city is much more French... but again, if you don't need to work... you would be fine... gosh i would love to retire at 51 LOL
Quebec city is tiny... a few hundred thousand people... it's very pretty but it's a bit secluded... i wouldn't recommend living there permanently for an American. A lot of Americans though are buying property there because they love the European cachet of the town...
Montreal is much bigger with the greater montreal being around 4 million people... so you can see that there is a lot to do and to see.. it's place to all the summer festivals and happenings... it's a wonderful place to live for open minded people who want to live freely
Perhaps you should plan an extended visit in montreal.... we are getting skate canada (laval across the bridge) next year and worlds the year after... so you could perhaps combine skating and a few more weeks of living, trying to be a local
I know you are from California... i have also lived on the west coast.... weather sucks in montreal.. it's very cold in the winter and it's way too hot and humid in the summer... extremes... i was used to milder oceanic climate and i hate it here... so if you are a very outdoorsy person, it's not fun... culture is indeed wonderful. Fine dining is great... I am not sure how easy it is to immigrate but perhaps if you tell them you love Patrick Chan it may help

The Province of Quebec privileges francophones but if you don't need to work you may fit in another category... or you could simply immigrate to Canada in general, like Ottawa, and once there just move to Quebec LOL... I don't think that immigrants have to stay into their home province forever. I am Canadian and I had to go through a lot of paper work when I changed provinces, for healthcare and what not... you should properly get an immigration attorney to save some time and worries.