It's a big country so need to know more about where you are looking. 

Tampa, the main seat of Hillsborough county, has seen a cool off just like the rest of the country and getting a 4 unit in that price range is attainable.As you mentioned, you first want to buy a place to live in; this could be the perfect setup: live in 1 and rent the other 3 out to cover your mortgage and maybe even have positive cash flow.

This is a topic I don't know anything about (because I've never tried to buy a property outside my country), but I'm wondering if the sellers know that you're in Canada, and whether that would potentially turn them off? 

The largest purchasers of single-family homes in the country are large corporations. 

I'm not concerned about the purchase process or managing from across the country, but I am wondering if there is anyone here that has been able to renovate and furnish their STR property from another state.

Hi Kyle,San Diego is a great spot, there is great spots ALL over the country as well to invest. 

Also, I live in an area that is one of the fasted growing areas in the country (Cary NC) and although it would be great to buy here, prices are pretty damn high and the cheapest multifamily I can find is 500,000+.

I have started just looking in various areas around the country to see where I really want to focus on. 

I am looking for a CPA who is very familiar with STRs in Santa Rosa country, FL.

I traveled the country looking for bad guys.