Also, you'll want to run a few different scenarios on this given the relatively small loan size.

Maybe run a black friday special :)

And if it is a misuse of the inspection contingency, aren't wholesalers who do this running the risk of being sued and even being forced to purchase the property themselves? 

I think guests hardly ever damage things intentionally, but when you have luggage coming in and out all the time and little kids running around a "new place," there IS a lot more wear-and-tear, scuffs/dents/scrapes, and broken glass. 

A property owner that is looking to maximize return may want to run their own STR.

Running the numbers can be deceiving at first.

Running numbers on a spreadsheet and in a BP calculator every day for ten properties when you have never seen one in real life or smelled mold or been to a hoarder's house or seen a structural issue is just procrastinating.

- Appears you are allowing the tenants to run the business, not the other way around. - We do not answer the phone outside of business hours.

If there is no HOA because it has been family run, it will be dicey, but generally if it is a private road, all those on the road are collectively responsible for maintenance and improvements.

As others are noting, it's important to run your numbers and would probably only recommending pulling from the HELOC for short term opportunities.