Contact several local property management companies, they should tell you a conservative and accurate rental amount.

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

And a refinance in the future is likely (our government can't manage the country with high rates for extended periods). 

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.

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.