I think in very specific markets this is doable.. 

If you're targeting a specific market, I suggest connecting with local investors through meetups. 

I would think your insurance agent might have access to some historical information for a specific area as they would want to examine this closely for their underwriting.

If you live there you probably have a good handle on the subtle market dynamics.One significant risk of buying any property out of state is that you have a lot less knowledge and first hand experience with all the nuances of that specific market.

And just the other day, I was grabbing coffee with a friend who reps a group of invsetors out in San Antonio.. they got burned early on by not clarifying their rental criteria, picking up a triplex that sounded good on paper but turned out to have a revolving door of problematic tenants.A baseline business plan isn’t just a mind-numbing exercise.. it’s the guardrail that keeps your momentum from swerving off into the ditch.

That is MUCH more useful than screening criteria. 3.

Are there any tools, websites, or resources you’d recommend specifically for real estate investors in Ontario?

Most foreign buyers are high net worth individuals who want to park their money there in a safe haven and they don't need BP.No restrictions apply to American buyers in the countries they'd generally want to buy, including those mentioned by Federico and many other popular countries.When it comes to Spain specifically, some more conservative banks will ask you for a 40% downpayment (that would be the maximum) but that isn't the rule.

By focusing your efforts on a specific area, you’ll be able to learn all the nuances and make more informed decisions.Best of luck with your investment journey!

Quote from @Austin Wolff: Hey Kegan, I published on article on BiggerPockets specifically to answer this question for people like you (and selfishly for myself):The 10 Best Markets for Your First House HackNone of the states you mentioned are on this list, however.