Hey @Jeff Ryan - While I can not speak to your exact situation, I can speak to the thousands of homes I have walked here in Chicago, where majority of the homes were built in the late 1800s/early 1900s.I would say that 7/10 of the older homes I look at have some sort of settlement in the foundation, which causes the cracks and sloped floors you are mentioned you are seeing in your property. 

Regarding Chicago, the 2024 property tax re-assessment in Cook County should cause some inventory to hit the market, specifically on the mixed-use and multi-family side of things which will be hit especially hard.

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

Huge plus side is it’s free so if you hate it no harm no foul.  

If they find out the truth later, it will cause distrust and resentment. 

Landlord can require tenants to be responsible for separately metered utilities, so can avoid waste.Landlord can get annual small increases in rent.NegativesMost of us don’t treat something we get for free the same way we treat something we’ve worked hard to obtain.S8 applicants claim “broke” and don’t like to pay application feesSame goes for security depositsS8 tenants, in our experience, tend to cause more property damage than non-S8 tenants. - Make sure you get a security deposit and perhaps do a surprise inspection of their current home.S8 requires an inspection (mostly health & safety) before approving a lease and then annually thereafter. - Not something most landlords taking care of their properties have to worry about.There are limits to clauses they allow in your lease.

This could cause gapping.

In addition if I paid a tenant to $crew me, it may cause me to lose sleep.

As mentioned if the holding company is not solely holding or owning assets together funneling monies as a loan would further complicate if there is a default but also cause you to file extra tax returns = $...Yes you are taxed on interest income or any money that you make, does not matter how you structure it, what comes into play is not how much your taxed but how much you pay someone to figure out for you how much you need to pay and each layer is an added cost. 

IMHO; UD actions are preventable actions caused by tenants failure to vacate the premises.