As professional property managers in Fort Myers Beach, overseeing a large number of beach rentals, we understand that 99% of guest stays go exactly as expected: a smooth experience with no issues at all.

However, there’s also that small 1% that will probably give you a headache.

How do you identify them early in the game? We’ve noticed that this type of guest often starts by asking many questions, sometimes rather specific ones.

Let us tell you a story. We recently had a guest who fit this pattern. We grew suspicious right from the beginning when questions began to pour in:

• • “Is it possible to check in early?” (a classic)

• • “What temperature does the hot tub reach?”

• • “How close are the neighboring properties?”

• • “Could you please specify the toiletries provided and their quantities?”

• • “What’s the ply count on the toilet paper?” (yes, you read that right)

• • “What is the thread count of the bed sheets?”

• • “What are the spices available in the kitchen?”

Once we answered what we could, we began to wonder how demanding and troublesome this guest might be once they actually checked in.

When the questions stopped, the guest booked, and soon enough they arrived. It was radio silence then, even though we sent a sequence of messages, including the door code, check-in and check-out instructions, and so on.

“It’s the calm before the storm,” we thought.

When the stay ended, we placed bets on how soon the call from the cleaners would come, announcing a big disaster. When the call finally came, we were shocked – and so were the cleaners. But not for the reasons you’re thinking…

It turns out that the cleaners found every drawer meticulously organized. The spices were not only straightened but also organized in alphabetical order. The hot tub, which had been slightly off center before, was now perfectly positioned on the deck.

We can only imagine that this was Monica from ‘Friends’ who had booked the rental just for some fun cleaning and tidying up.

Whoever this tidy fanatic was, though, they were a fantastic guest, and we’d welcome them anytime! Boy, have we learned a lesson?

Judging a book by its cover isn’t always the best approach in the short-term rental industry. (But hey, we still reserve the right to exercise caution when we’re talking about college groups booking for spring break. Just to be safe!)