Its important that you go with the plan that makes the most sense for your facts and circumstances  

It's your job as the investor to project the other expenses, based on how you plan to operate the property.

I also  plan on doing a check in check out sheet similar to that of our long term rental in case any damages they would be liable as well.   

I plan to research more on the MTR space.

The exercise of tracking it regularly helps to keep it top of mind and it also allows me to see how my plans are working compared to my goals and if I need to make adjustments (I agree with @Chris Clothier that you've got a keep a long-term perspective because real estate investing, like life in general, is a marathon not a sprint).Great question, Allan!

Seems like this would make a great business plan if it was even possible

Come up with plans on how to deal with these risks if they come up.Connect with local real estate professionals, Airbnb hosts, property managers, and investors to gain insights from their experiences.

Rented my house we originally lived in 12 years ago because we couldn’t sell it when we moved and that’s how we got started. 5 years ago we made a plan and an effort to accumulate multi family properties and did that.

Plus a lot of general public started doing that which is the signal for the end... kinda like a good night club going down hill.Moreover, the tax implications for vacation home rentals vary based on how often the property is rented out and used personally.

Getting into a property that has negative cash flow can seriously hurt, even if you've thought out a magnificent plan for it.