I'd expect prices to continue to appreciate, so the longer you delay, the more expensive things may be. 

Finally, of the extra $200k, how much are you putting into operating reserves? 

Faced with mounting expenses, extended timelines, and diminishing returns, we ultimately decided to sell the property instead of continuing with the BRRRR strategy.The Insurance Mistake:The biggest lesson I learned was that I had the wrong type of insurance.

<<< Correct, that is exactly what I am referring THIS IS your tradeoff most of the time when using turnkey companies AND WILL CONTINUE to be your tradeoff even when using a realtor IF YOU DON'T VERIFY YOUR NUMBERS. 

So purchasing larger and larger properties allows investors like Benjamin to purchase more depreciable basis while continuing to defer and recapture.  

(Gas are more expensive to buy, but cheaper to operate.).

Hi Randall-Congratulations on buying a rental property well back in 2020.I am sorry to hear the property is now cashflow negative $200 a month.Your question is should you sell or continue to keep it with the negative cashflow.Depends on your personal goals and if being negative $200 a month plus any unexpected repairs or vacancies is affordable to you, but if you can solve the negative cashflow by turning the property into a furnished mid-term rental, for example, your future self may thank you.To Your Success!

The main reason for this is to continue to do medical missions around the world  even when I'm dead.

I'm also concerned about the liability that I might be exposed to here by allowing what appears to be a business to operate out of my rental.

You can check the NMLS for licensing (some servicers will operate without being properly licensed in that state).