However, I haven't been able to find any official information confirming whether this is legal or if it violates any laws.I'm hoping someone here might have experience with this or know of a reliable source that can clarify the legality of contacting a tenant's commanding officer.

I assume it's the "Friends of BP" group since there's nothing really other than official stuff on the BP page.

The designated responsible party must be available on-site to address any issues as soon as one (1) hour following notification from an occupant, a city official, a code compliance officer, or law enforcement officer.Prior to the city issuing a certificate of registration, the vacation rental is subject to inspection to ensure compliance with: (1) minimum safety requirements under section 34.5-12; (2) minimum information requirements under section 34.5-13; and (3) to confirm compliance with Chapter 34.5 generally as well as any other applicable provisions of the Sarasota City Code and Zoning Code.The minimum safety requirements are set forth in section 34.5-12 and include compliance with the Residential Swimming Pool Safety Act, operation of smoke and carbon monoxide detection systems, and installation of fire extinguishers.The minimum informational requirements are set forth in section 34.5-13 and include, among other things, providing: (1) the location of the nearest hospital; (2) the non-emergency police telephone number; (3) the dates and approximate times of trash and recycling pick up; (4) the street address of the vacation rental; (5) the name and phone number of the designated responsible party or parties; and (6) emergency evacuation instructions.

Those going unemployed won’t be reflected in the official figures., c.  

Would have to call and order an official payoff from the lender 

you need to send an official notification to everyone.

The official source I was able to use is the National Association of Realtors site and it shows Multi-family market cap rate of 6.1% for 2024 Q1 (2023 Q4 was 5.7%).

I have a year-round renter in the basement as well - it’s not converted as a duplex officially, but has two exits and street level entry.

The seller who signed these leases would typically handle, and if it is not completed, then the lease is not official, as there are still contingencies for lessee to cancel if TI is not completed, presumably.3: Why are you paying any of the agent commission?  

It’s also annoying that you can’t obtain official cc&r rules until offers is accepted which is a waste of time!