So, for MD, this seems to fall under usury law, which makes sense. 

I'm doing my 2023 taxes (late) and we had some siding and gutters put on in Fall 2023, however we did not pay for it (~$13,000) until summer 2024.

Then you should be able to sell for above market - unless rates fall thereby potentially wiping out the 20% even with assumability.   

For example, do you need a permit to swap out windows (lead renovation EPA requirements for the age of home or do you need tempered or fall protection) all the way to a city that has $3,000 permit fees. 

Even a tree falling on the property or fire would not be covered, if they found out you "broke" the policy agreement by using a landlord policy for a STR. 

These variables can cause deals to fall through or add unnecessary stress to your project—something you don’t want to experience as a new investor.Better Negotiating Position: Cash is king in real estate.

If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

In Florida, this situation falls under our Unlawful Detainer statute.

I was practically fully booked all Fall and Winter.

I use a scoring system where applicants gain and lose points and their total either meets or falls short of my established line in the sand.