I have used two companies, and while they are both more expensive than regular insurance, they have extra coverage that is specific to STRs.  

Based on all the facts and circumstances, you participated in the activity on a regular, continuous, and substantial basis during the year.

Check the in person events and meetups in your local area, our online community is full of knowledge and folks willing to share and still nothing replaces the opportunity to interact IRL, you never know who you will meet and where that can take you on your REI journey.

We have clients that have used FHA regular and 203K loans in areas that they would not necessarily want to live forever, but it was a means to an end. 

Do a regular lease.

Inspect regularly.

Given my tech and data background, I'm considering developing an online app specifically for Canadian investors.I'm envisioning an interactive dashboard that integrates economic data, sales figures, bylaws, and rental information, complete with prediction models.

Starting my real estate investment journey and using experience as a budding commercial/residential agent to guide my journey as well as the journey of others I interact with.

I find investors are just as much work and sometimes more than a regular buyer and seller. 

More than likely, your Landlord goes down those roads on a regular.