You just have to weigh the risks and choose whichever you are confident with.

You would need to choose between what is more important.... owning the listing or owning a STR that is dominating the market it's located in, by maximizing the tools available to manage the property.

Best of luck with whichever path you choose!

While it is most common for SFH lawns to be tenant-responsibility, we are offering a weekly mowing service for $100/mo due to being such a large lot, if applicant/tenant so chooses. 

Most importantly, choose a market that aligns with your goals!

But, if you choose to buy on your own then yes you can ask for financials directly from the seller.

I think an issue you will run into is how many Canadians choose to invest in the U.S. and therefore us the U.S. tools.

Airbnb has several options to choose from (Flexible, Moderate, Firm, Strict and Super Strict). 

I wasn't required to have higher liability coverage and I didn't choose to do so but something to talk with an insurance broker about!

Not as many “qualified” tenants to choose from.