♥ Love Letters ♥
Personal ads, open letters, honest invitations.
Operator-to-operator, the conversations the conferences never quite get to.
No. 005 · July 25, 2026
Dear operator, it was never 15.5%
A love letter to the manager doing fee math in their head at midnight
Raise your rates 15.5% to cover Airbnb's new host fee and you're still short $2.40 on every $100. Here's the number that actually breaks you even.
by Billy O'
No. 004 · May 21, 2026
Four great ones.
A letter to the operator who can't find good people.
73% of property managers say staffing is their #1 barrier in 2026. The labor market isn't broken. Our hiring philosophy is.
by Julia Daly
No. 003 · May 15, 2026
Why the Front Line is Not for Robots
In defense of the messy call
Do we really want our guests talking to robots so we have more free time to talk to robots?
by María Eugenia Jacobsen
No. 002 · May 14, 2026
Pull Up a Chair: Why Atlanta Needs a Real STR Community Supper Club
An open invitation to Atlanta's hosting community
There is something powerful that happens when people sit down at a table together.
by Mateo Bradford-Vazquez
No. 001 · May 11, 2026
Motellier seeks long walks on the beach (hand holding optional)
An open letter to my fellow operators
I'm a 40-something innkeeper, STR manager, designer, leader, dirtbag runner, currently operating across eleven states and two countries.
by Billy O'
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About the author
Billy O'Sullivan
Principal · Ohana Vacations & Ohana Inns
Operating boutique inns, motels, and short-term rentals across Hawaii, Maine, Oregon, Colorado, Idaho, Utah, Arizona, Vermont, Georgia, and Costa Rica. Co-founded Ohana Inns in 2020; previously CEO of ALTIDO. Writes The Check-In because the conversations operators most need aren't happening anywhere else.
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Five headlines, one pro tip, dream-weaving, and a press-play pick. ~5-minute read.
Issue 010 · Saturday, October 17, 2026
Vrbo flattens its commission, Oregon writes a new line onto your receipt, and the rules database our industry still doesn't have.
Ten towns changed their STR rules in four days. We'd like to start fixing that — in the open.
Issue 009 · Saturday, August 15, 2026
Costa Rica's rainy season forgets to rain, Cambridge second-guesses its own cap, and Longmont gets its first boutique hotel.
Plus: why the driest Guanacaste in years might be your team's best excuse for an offsite.
Issue 008 · Friday, July 24, 2026
DC opens hosting to its renters, a billion dollars pours into hospitality tech, and the market quietly rewards whoever stayed put.
Plus: why your listing should speak to three guests, not one.