I pivoted to doing creative financing.

I have one in mind at Rent to Retirement. 

For another business I run I do post daily accountability in a FB/mentorship group and that does help me stay on track.

Keep in mind the more you write off the less money you will show as you net.If you have (2) full years and depending on how the accountant files your taxes you will have a schedule C more than likely or another schedule that shows profit and loss.

Is there debt on the property or are you doing all cash?

Buy the house and loan her the money. 

All of this information should be available online so you'll just want to make sure you do your research. 

Now as I stated I'm not a agent but I do feel confident in this here friend. 

Neither VRBO nor Airbnb are vetting guests, either.The best you can do is have some internal controls, such as minimum number of nights.

Then I save that amount each month in reserves until I need them.