Couple things for Travis to consider...Canadian stations have hired Americans rather frequently, and vice-versa, although if you're moving north it helps if you have family ties in Canada that could get you a Canadian citizenship certificate. And if you get an offer from Toronto, you'll make big bucks, close to what you will get in Chicago (which is about the same-sized market as the Greater Toronto Area). Vancouver? Comparable in pay and benefits to a top-20 market, pays a lot like Detroit or San Diego.
What you may be disappointed to find out (as I found out when approached by a couple of Canadian stations in some rather large markets including Hamilton and Ottawa) is that the money's not as good as you might expect. A top 10 or top 20 Canadian market may be no bigger in population, or ad revenue, than market 50 in the U.S. That means salary and benefit packages will be no bigger than the top-50 market where you've been working in the U.S., and the cost of moving alone makes it a questionable sideways move. Life in a Canadian market is nice, you make as much as a market of similar population in the US, especially these days when the currencies of the two countries are within a few pennies on the dollar of par. But you need to compare the markets you're moving to or from by the numbers--specifically by 6+ population and ad revenue--to see if you'll really do better moving in either direction across the border.
Another thing for Travis to consider; there are markets within a short distance of your own home, places like Las Vegas, San Diego, Sacramento, of San Francisco/Oakland, that are just as desirable places to live, and just as attainable, as a comparable Canadian market. Why not think about the markets you know, closest to you?
I wound up opting to stay home rather than making a sideways move in my own career just for a change of scene, and have never regretted it.