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Your owner statement is why they left. Not your occupancy.

26 automated guest and owner messages, mapped end to end — every trigger, every branch, and the reason each one exists.

Pulled from a live 32-property portfolio across California, Arizona and North Carolina. Every private detail stripped. Use it, edit it, rebrand it.

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26
Automated messages,
mapped end to end
Free download
  • → Every trigger and interval
  • → The conditional branch, explained
  • → Channel splits that keep you compliant
  • → A six-message owner track
  • → What each message prevents
As heard on Boostly Podcast Direct Booking Simplified Angel Host Featured in SD Voyager

Why this exists

Most message packs are a folder of nice-sounding texts. The copy is the easy part.

What moves your review score, your direct-booking share and your owner retention is the architecture — how many messages fire, exactly when, which ones branch on a condition, and which are deliberately different per channel.

So every message in this system comes with four things: the trigger, the channel it sends on, why it exists, and what goes wrong without it. Read the why before you copy the what.

4.62 Average rating for large property management companies. Individual co-hosts average 4.86. Airbnb, published data
18% Of operators with a direct booking site get literally zero bookings from it. Hostaway 2026 STR Report
84% Of managers with 100+ listings already use AI. Across the industry it's 61%. Hostaway 2026 STR Report

What's inside

Six stages, 26 messages, 26 pages

4 messages

Booking & confirmation

Fires within minutes. Sets three expectations before they can become disputes — check-in time, early check-in, and packages.

8 messages

Pre-arrival

Three escalating reminders that only send if the guest hasn't completed the portal, plus two upsells that exist purely to make money.

3 messages

In-stay

The review-protection message. Invites complaints while you can still fix them, and teaches the star scale before they rate you.

3 messages

Departure

Checkout instructions, the five departure tasks that save a same-day turnover, and the review ask at peak goodwill.

2 messages

Win-back

The cheapest direct bookings you'll ever get — at checkout, and again at 60 days.

6 messages

The owner track

Messages that exist only for owners. Almost nobody under 60 doors runs this, and it's the least expensive retention work available.

Fit

This is for managers, not hosts

Built for you if…

  • You manage other people's properties for a fee
  • You run somewhere between 5 and 60 doors
  • You've got a PMS and you're not using half of it
  • Your owners hear from you less often than you'd like to admit
  • You'd rather see the reasoning than be handed a template

Not for you if…

  • You're looking for your first co-hosting client
  • You want arbitrage or buy-to-STR strategy
  • You want interior design advice
  • You manage one property and message guests by hand
  • You want someone to tell you which software to buy

Who's behind it

By operators, not gurus

Doors & Data is run by Al and Elissa Sedighravesh. We own and operate Rather Be Properties, a five-star vacation rental management company running 32 properties across California, Arizona and North Carolina.

Elissa spent a decade in five-star hospitality at premier resorts in Australia and Dubai. Al came from twelve years in residential real estate and finance. We launched our first property in November 2021 and have been figuring this out in public ever since — including on the Boostly Podcast, Direct Booking Simplified, and Angel Host.

Everything published here comes out of a portfolio we actually run. When something didn't work, we say so — and there's a fair bit of that. We'll build paid tools in time. The reasoning stays free either way.

Operating sinceNovember 2021
Portfolio32 properties
MarketsCA · AZ · NC
FocusOwner acquisition · AI · direct bookings
Software allegianceNone

On the record

Under two minutes of us getting it wrong in public

Recorded for the Boostly Podcast in October 2022, back when we ran four properties instead of thirty-two. We've left the mistakes in, because the mistakes are the useful part.

0:29

Why we built it

Two daughters, a phone that never stopped, and the decision to build for leverage instead of income.

0:27

The year we left 10–15% on the table

We ran our first property for twelve months without a pricing engine. Al puts a number on what that cost.

0:54

The cleaner charging 30% over market

Nice guy, complained constantly, priced well above the market. What replacing him with a dispatch system actually returned.

Start with stage three.

The post-check-in message is the highest-return single automation in the document, and you can have it live today. The other 25 can wait.

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