I can't imagine Rockford being a destination.

Many of the virtual assistants that I have hired have told me stories about getting yelled at constantly (one worked at Comcast, if you can imagine) and almost all of them have had stories of either not getting paid, or not ever knowing when they would get paid.

You'll also want to have plenty of your own capital in reserve to deal with vacancies and repairs.I imagine a lot of the tenant-landlord problems can be prevented by providing good customer service and having clear standards, both in who you rent to and how you maintain your property. 

A lot less and better quality, I’m in Detroit you can imagine all the junk the big three brings here and making low quality cars.

The point is, if you can break even now with high rates, imagine another future refi to lower rates and making positive cash flow again.

There are also a  couple of things you could do on Airbnb to fix this, the could transfer funds from the rentals into your account, you could take over their account momentarily but I imagine Airbnb frowns upon that.I think the pro/cons are the same as any other property you buy that is already occupied.

He imagines just us and our family.

People felt invaded by putting a picture of their property on the card and I can imagine they would feel the same way with you putting a picture of yourself in front of their house. 

As you may imagine, there are good and bad and you can not tell by the pictures you see.

I lend money privately and would never consider this as it is dependent on things out of my control (permits, neighbors, you being a good host, rental demand etc) I sell a ton of STR that are in actual resort communities and have great amenities and they are all  competing for the same guests, I can't imagine that there is a need/demand for this type of unit.