I totally agree with your point that if the property burns to the ground next week, and you have two different underwriters with liability -- one to you, and one to your wrap buyer -- neither insurance company will want to pay a penny.

They placed me with Burns and Wilcox.

Move-Out Checklist for Investment PropertyA well-structured move-out checklist helps protect your investment, ensures a smooth tenant transition, and reduces turnover costs.Tenant Responsibilities (Before Move-Out)✅ Provide written notice of intent to vacate (per lease terms)✅ Schedule a move-out inspection (if required)✅ Pay all outstanding rent and utilities✅ Remove all personal belongings and trash✅ Clean the unit thoroughly:Wipe down walls, baseboards, and doorsVacuum and mop floorsClean kitchen appliances (inside/out)Wipe down cabinets and countertopsScrub bathroom sinks, toilets, showers/tubs✅ Replace any missing or burned-out light bulbs✅ Repair any tenant-caused damage (holes, broken blinds, etc.)✅ Return all keys, garage remotes, and access cards✅ Provide a forwarding address for the security deposit refundLandlord/Property Manager Responsibilities✅ Conduct a pre-move-out inspection (optional)✅ Take photos/videos of the property’s condition✅ Verify all keys, garage remotes, and access cards are returned✅ Check for unpaid rent, utilities, or damages beyond normal wear and tear✅ Hire a cleaning service (if needed)✅ Complete repairs and maintenance (paint, flooring, appliances, HVAC, plumbing)✅ Change locks if required by state law or property policy✅ Test smoke detectors and carbon monoxide alarms✅ Review lease terms for security deposit deductions✅ Send tenant security deposit refund (minus any deductions) within the legal timeframe

Did you overreach on a project, get burned by a client, or misjudge a contractor?

After quitting the RE space in 2008 as a burned out landlord with upside down properties, I rejoined the space as a curious vacant land newbie investor in early 2023.

A rider allowing for using your owner-occupied property as a short-term rental for a specific/limited amount of time is very different than an investment property being used as a short or long term rental 100% of the time.Also, telling your home insurance company that you STR your home occasionally does not give you extra coverage for those types of risks, it simply means if your renter burns your home down the insurance company isn't going to immediately deny your claim. 

Quote from @Brook Burns: Thanks so much for the recommendations!

It is something that gives you the leverage to make more money and have the ability to not pay the debt on it monthly either (your burn rate on it). 

It could be anything... a mistake in estimating, a cost overrun, or something like the place burns down and the insurance wasn't properly taken out, or theft (of the money outright) or theft of materials along the way.    

So make sure if you also want to collect last month's rent up front to not get burned, document that!