The homes are typically brick ranch style and need some updates. 

The problem is that there are no limits on how many short-term rentals a single property owner can operate, he said.In some Arizona cities, Drennon said, “bad actors” are buying and converting entire apartment buildings into Airbnb rentals, effectively creating hotels in residential areas and depleting local supplies of rental housing.By contrast, traditional hotels typically operate in commercial areas that have much higher property tax rates.Many cities around the world — from Paris to New York City and even Airbnb’s home city of San Francisco — have laws that limit short-term rentals to protect the hotel industry and residential neighborhoods.

How old of an appraisal will a conventional bank typically accept?

Any reference's and / adviseThanks @adrianwilliams

@Ken Catron My understanding is she could get a 5% down type of loan, but typically banks and all lenders want to know you will occupy.

What is a typical payout schedule to these private investors? 

When you mention hiring, are you referring to the owner or PM hiring a bookkeeper?  

I was a Personal Banker before that which gave me some good exposure to lending, primarily doing refinances and referring new purchases or larger deals to a mortgage partner.

Id say the issue here is a little more shady than your typical transfer of a property into an LLC. 

These types of properties typically only trade when the market is nearing the top, making it a challenge if forced to sell.