My questions are: 1)  Should I have them sign an agreement for a 4 night stay, when they've stayed previously without incident? 

If I just made enough calls, walked enough properties, and hustled enough late nights, I'd be successful. 

The good ones notice right away and feel safer.Community touchpoints: Simple BBQs, pizza nights, or coffee mornings help residents connect and shift the culture fast.Reputation boost: Ask your good tenants for updated reviews—offer small gift cards as a thank you.

This is how many investors lose their shorts, so don't risk this with a stranger you've never met who can easily ghost you and disappear in to the night forever, make the trip. 

If you're in Nashville, there's an investor meet up happening October 29 at Monday Night Brewing.

If you want to keep earning the same amount as before, you can slightly raise your nightly rate to cover the 0.5% increase.Example:If you charge $100 per night, Airbnb used to take $15 (15%).Now they’ll take $15.50 (15.5%).You’d earn 50 cents less per booking unless you raise your price a bit.So you could adjust your rate to $100.50 or $101 to keep your income the same.The issue is most of us are setup on the Airbnb setting where the guest pays 10% to 15% and we as hosts pay 3%. 

What are their nightly rates, occupancy and amenities?

Currently I’m operating it as a STR, but I need a new cleaner and the quotes I’m getting are in some cases double my nightly rate, and the amount it grosses is only slightly more than what it will do as a LTR.

In practice, most operators (including platforms like PadSplit) operate successfully without specific licensing because these homes don’t fit the typical short-term rental model—average stays are often six to eight months rather than nightly or weekly.The benefits of this strategy are clear: it helps create affordable housing options in a market where affordability is increasingly scarce, and it fills a short-term housing need for working professionals, students, and those transitioning between life stages.

But it’s fun to stay in it once a year for a couple nights when we go to Branson.