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Maybe Old School Had It Right

August 31, 2026 6:30 AM | Rebecca Gallagher (Administrator)

Good morning!

I spend a lot of time hearing about the newest technology that's going to make STR ownership easier.

AI. Smart locks. Noise monitors. Dynamic pricing. Automated messaging. Digital guidebooks. Property management software that can practically tell you when a lightbulb is thinking about burning out.

And I love this stuff! Anything that makes us better, faster and more efficient is worth exploring.

But lately I've been wondering if, in our rush to automate everything, we've forgotten that sometimes old school just works better.

Think about it.

A perfectly timed pre-arrival text is efficient.

But a handwritten note sitting on the kitchen counter saying, "Welcome! We hope you have a wonderful weekend!" feels different.

A digital guidebook can put hundreds of recommendations at a guest's fingertips.

But there's something charming about flipping through a well-done guest book on the coffee table, especially when you've scribbled in a few personal favorites.

You can install cameras and noise monitors to help protect your relationship with your neighbors.

Or you can also walk next door with a plate of cookies, introduce yourself, give them your cell phone number and say, "We're going to be renting our house. If there's ever a problem, please call me."

Which neighbor do you think is more likely to call you before calling the township?

And this goes way beyond guest experience.

We have automated maintenance systems—but there's tremendous value in having a maintenance person who knows your house well enough to notice the loose railing before a guest submits a ticket.

We have Facebook groups, WhatsApp chats and Zoom—but sometimes nothing replaces sitting across the table from another owner and having a conversation.

We can email township supervisors—but introducing yourself, shaking their hand and building a relationship before you need something from them is probably worth 100 emails.

We can even use AI to help us write thoughtful responses to guests.

But when somebody is really upset?

Pick up the phone.

So... Old School or New School?

I think that's the wrong question.

The answer is BOTH.

Use technology to eliminate the repetitive stuff.

Automate the things that don't need a human.

Use software to make your team faster, smarter and more consistent.

Then use the time you saved to be MORE human—not less.

Write the note.

Make the phone call.

Walk next door.

Shake the hand.

Show up in person.

Remember the anniversary.

Ask the guest why they're visiting.

Thank the housekeeper personally.

Get to know the township employee you've been emailing.

Because in a world where practically everything can be automated, the things that aren't become increasingly valuable.

Technology can make you more efficient.

Old-school hospitality can make you memorable.

And maybe the STR owners and operators who really set themselves apart will be the ones who figure out how to be really, really good at both.

Have a great week!

~Rebecca

P.S. What's one "old-school" thing you still do in your STR business that you'll never automate? Hit reply and tell me—I have a feeling there are some GREAT ideas out there.

P.P.S  Have you signed up for the STR Advocacy Summit yet?  What's stopping you?!


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