What may actually be helpful to a family (stability) is not what regulators look at.

Is it tied to changes in the market, a response to new regulations, or part of a long-term plan?

Account ClosedAdding your property manager as "additional insured" is standard practice and beneficial for you.

Start by educating yourself with foundational books like The Millionaire Real Estate Investor and practicing deal analysis using tools like BiggerPockets calculators.

Quote from @Ashish Acharya: @Sanjai Dayal If your LLC owns the commercial building and leases space to your medical practice LLC, it’s essential to charge rent at fair market value (FMV) to avoid IRS scrutiny.

Pick up the phone or stop by local code enforcement offices to make sure that you have a crystal clear understanding of local laws and regulations.

As with most municipalities and jurisdictions, the evolution of the AirBnB market has spawned regulation and restrictions on where, when and how a STR can operate.

That would bypass many city/state regulations that force landlords to rent to people here illegally. 

Heck, even within offices, the small 1-tenant office buildings suitable for a dental practice or law practice, those are in a very different world. 

Wholesalers are not regulated by Real Estate Agency, therefore not required to abide by certain laws and disclosures.