Quote from @Doug Stankavich Stankavich: Update from my limited experience: My brother-in-law no longer works there due to very confusing and shady communication or lack thereof. 

Excessive complaints or three violations in three years could lead to losing the ability to operate​.Impact on Neighborhoods: Non-owner-occupied STRs (Type 2) may cause friction in residential neighborhoods, as they often function like businesses, which can disrupt the local community atmosphere.Recent Regulations (2024 Updates):1) STR operators must obtain a permit for either Type 1 or Type 2 properties, depending on whether the owner lives on-site.2) Platforms like Airbnb are required to remove any listings that lack a valid permit.3) New noise and occupancy regulations apply, with stricter enforcement through permit revocations and finesThese regulations are part of the city's efforts to balance the benefits of STRs with the preservation of neighborhood quality and local safety standards.4o

Also - you probably wouldn't want to close on the property without insurance as you would also lack protection.What is the reason you can't secure insurance?

The complete lack of understanding is going to do some folks in.The world has a way of working; you reach, it'll teach.

There is a lack of good management options up there so I manage myself.

Section 8 Homeownership Vouchers (TOTAL) DefinitionSection 8 Homeownership Vouchers refer to housing subsidies received under the Housing Choice Voucher homeownership option from a Public Housing Agency (PHA).Required DocumentationThe Mortgagee must verify and document the Borrower’s receipt of the Housing Choice Voucher homeownership subsidies.

Hostaway's lack of transparency in their pricing makes them pretty hard to recommend to anyone since these types of "custom" pricing schemes are often used as a means of upcharging new customers. 

If he doesn't want to apply or can't pass your screening due to the lack of SSN, then tell him he can't apply.

I think you're right, the lack of control is probably going to be your biggest emotional hurdle.There may be some middle ground that softens that blow up. 

Their lack of excuse really doesn't change anything because this isn't or at least should be personal to you.