The first couple is a no-brainer.The second group has too many people, increasing wear-and-tear on the home.

By accelerating your depreciation schedules, you reduce your taxable income which in turn increases your operating cash flow.

The lower barrier to entry would be excellent for my personally smaller net worth.

I will mention that a hot tub could really increase the frequency of bookings. 

Whether or not you believe there will be drastic changes, we are already seeing increasing weather events with unusual patterns like the hurricane that whipped through Central (Inland) Florida in 2024.

A furnished mid-term rental or month to month lease can be well worth the small incremental monthly cost for this flexibility if you are serious about finding a great live in flip candidate on your timeline, not that of your employer's. 

Thus increasing density ratio.

My spreadsheet also includes FMV of every property so I can monitor appreciation, year over year comparison of tax & insurance increases, current rent & last increase & last amount, etc.

This demographic is projected to keep increasing over time, so I would do whatever you can to hold onto this property (ie cash flow well).Furnishing 700 sqft with PB or West Elm (you and my wife would get along great, Bonnie) won't be price-prohibitive and well worth the cost.

The wrestling and wrangling you would have to do to collect would never be worth your time.