If you are spending this much time scrutinizing your guests, you may want to consider hiring professional property management!

If I only manage my holding company - no active PM role - does that help avoid filing/registering in NY?

Employee Management: Given the absentee nature of the business, how do you ensure quality staff performance and customer service in your absence?

Hey Mike, did you manage to find an insurance company for your str?

Since we manage our rental properties ourselves, I told him our rental LLC should be considered as a business.

Is it easy to find a property manager who understands the ins & outs of the section 8 process there?

Questions I'd have if I were in your shoes would be based around how the CAM expenses, management, taxes etc are going to work. 

House hacking will also give you some personal "property management" experience.

Management was negligent in that there solution for everything except the most dire problems was your rent is so cheap deal with it and nothing ever got done.

While we do not see income from these properties and are not managing them we do have a significant amount of depreciation and losses that have been assigned to us and carried over from the past couple years.I am invested in some growth/equity focused projects already and am specifically looking in reliable income focused strategies that are tax efficient provided the losses I have from my family.