I think in very specific markets this is doable.. 

Did you have specific questions or comments?

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

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.

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.

You need to research/know the rules, laws and regulations (including HOA if applicable), like you'd do in any US city.

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!

@Gregory SchwartzWhat specifically are you hoping the software will do for you?