And it's not only homes, it's all the infrastructure a city needs.On the insurance issue, I think this may be the end of national carriers.

I do agree the lack of control is a potential issue.  

So I wouldn't recommend them unless time isn't an issue for you and you don't mind waiting a few days for a response.  

RESOLVE this issue NOW and make a clean break. 

I doubt if you'll have any issue with your hold period since it is all about your intent anyway.

Since you’re considering converting the upper unit into a short-term rental, you may also want to implement strict rules around smoking or strong odors in your house rules to avoid future issues.

As others have stated this is unrealistic due to arrival time, cost order issues, and volume to make it worth it.

(other issue was a leaky toilet we took care of, at our expense).  

One issue that I'm noticing is the range of reported insurance costs.

If you currently rent for $2,500 and take the $1,750; you have additional positive cash flow of $750 for your rent situation.Have you thoroughly looked over the capex potential issues?