In a properly run platform, VRBO would require hosts to upload this information to the platform, and the guests would access the information directly from the platform, eliminating drama. 

I don’t know the condition of the property nor how to properly assess it considering my lack of experience – who would I approach due diligence?

When dealing with unique properties like this, I would make sure that the ADU on this property is properly zoned. 

@Joshua Melero We had vacant property that were remodeling and considered installing cameras inside the property.

I have used Obie and Proper; I haven’t had to make a claim with either.

Things such as location, condition, aggressive rent rate, etc affect how much work may be required to properly manage a property and its tenants. 

I’m waiting on a contractor to come install an egress anyways, so the extra month it’s taking me to do minor repairs and paint  hasnt affected the schedule yet, but it’s definitely an important lesson.

The registration site still isn't working properly.

But it's missing a couple of integral features, such as maintenance requests/tracking, and also my bank (which I do not want to leave) for some reason has always hated connecting to Stessa and thus never works properly...

I am now looking to get the proper STR insurance on the unit.