I think tax benefits should be secondary to buying something that would work well as a STR.I would recommend you consult a tax professional to see what possible tax benefits you could receive from buying this STR.

@Jared W SmithThe words trust but verify ring very true with those stories.

I'd talk to a tax professional in Canada. 

Hiring a licensed professional is many times optional - you don’t always need to see a doctor when you’re sick, and you can DIY a home remodel if you have the right tools and knowledge.

However, not one general location is going to help you determine whether it's a good market for multi family or single family etc.The one true way to start looking into a market is talking to an agent who knows the area.

One of the biggest challenges for everyone involved is being on the same page about the actual time required for maintenance.DIY landlords rarely properly track their time when it comes to property management in general - tracking their true time invested in maintenance is where they perform the worst.Investors that hire PMCs are rarely any better at understanding the true amount of time maintenance takes.

Looking to connect with an experienced tax professional regarding filings for my 2 STR properties (Gatlinburg & Hollywood FL) which were both recently cost segregated.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I know that true real estate investing is not get rich quick.

It’s crazy but no matter how nice and professional I make the photos look in the Airbnb listing for that house, I still always get comments from guests that it’s way nicer than they were expecting.