Depending on the area of the STR, another possible upside would be owning in an area that has different market fundamentals and may still perform even in contraction stages of the RE cycle.Having said the above, there is a learning curve to running a short term rental, and my experience has been, that there is also a period of getting the property running smoothly and getting reviews before it is running at its peak.

However I will let it slide as I just started Vikings today due to this list.

Leaning on a tenant to let this slide is not rude in itself, but it is also not ok for a landlord to let it slide if the tenant is unwilling and wants a heating system that meets standards!

I think you should buy the property next door to his house and use it as an Air BNB until you decide to move there.And in your counter claim to his law suit ask for a per cent of the take he will get when he does the "I was a con man, and now I am reformed and will tell you how to avoid being taken by a smooth talking con"  series of videos and conferences...since you are helping him come clean.

With that said, my willingness to negotiate and be flexible is also on a sliding scale of how many doors you own.

We didn't have the internet, all programming was by stacks of punched cards & calculators were banned during exams so we had to use slide-rules.

Once you’re mortgage free, it’s all smooth sailing.

Again, this is after the property is 6 months or older and running smoothly. 

And given his significant experience, he has a great team and systems in place to make everything run smoothly.

My contractor assigned a project manager and everything went smoothly.