Thanks Tom Wheelwright for writing the book "Tax Free Wealth". 

If a property can come close to breaking even then it's essentially "cash flowing" in my book. 

We target insurance and corporate bookings as well as travel medical professional agencies. 

., more than half of the calendar year) for the Borrower’s personal use and enjoyment"This means that you can only book it out on STR platforms for half of the year (50% max occupancy), which really sets a cap on your max income. 

The best way to get started is to pair books and podcasts on the topics you think you will be interested in first with meetups in real life.

(I'm in the middle of Brandon Turner's book Rental Property Investing.

You can find plenty of markets where nobody builds and you won't get competition but you won't get bookings either because there's no demand.It has been proven that, with short term rentals, it's the really professional hosts that make the bulk of the money (think the 80 - 20) rule.

Lastly my wife was a trainer for Floyd Wickman back in the day .. you maybe familiar with his Son Gino's motivational books.

If LL uses accrual method, they can book revenue without receiving.  

So as investing partners it makes sense because we will both have extra cash at the same time, we partner up to cut the risk in half + we both specialize in a couple things the other does not in terms of being a rental property owner (e.g. running the books + marketing vs actually fixing things).