No he would, just like most other people. They myth that those places are so much better would get destroyed really quickly after they moved.
The second part of your sentence makes sense to me. But you actually think that anyone who moved to Canada would "hate" it once they got used to it? I assume you've been to Canada. What secrets are they hiding behind their facade of being nearly identical to us?
Many Americans I have known who have come up here have noticed how safer Canada is, for example. I'm not going to list all the things that make Canada a better country though, as I need not want to offend y'all. I have been to the U.S. a few times, and I would rather live here. Perhaps there's some sort of emotional attachment (and isn't that what patriotism is?) or perhaps the cities in the U.S. I've been to are not a good representation of the country (Buffalo, Rochester, rural Virginia, etc.). Oh, I've also been to Vermont, but isn't that just Canada Jr. anyways?