♥ Love Letters ♥
Personal ads, open letters, honest invitations.
Operator-to-operator, the conversations the conferences never quite get to.
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 005 · Friday, May 29, 2026
Airbnb adds hotels, set-jetting picks new towns, and the small bag your guest opens in the driveway.
Plus: the Tuesday vendor text that drops same-day no-shows from 1-in-6 to 1-in-30.
Issue 004 · Tuesday, May 19, 2026
Booking goes alt, Vrbo rewrites Premier Host, and the bath sheet your guests are quietly judging you for.
Plus: the morning-of-arrival text that drops check-in fire drills from 1-in-3 to 1-in-12.
Issue 003 · Monday, May 11, 2026
Airbnb draws an AI line, the World Cup picks favorites, and hospitality gets a new word.
Plus: the night-before-checkout note that pulls 4-star reviews back to 5.