The CheckIn

A weekly read for the hospitality crew

The week in stays, told by the people who run them.

Five headlines, one pro tip, and a slice of dream-weaving for hosts, managers, owners, and the operators keeping this whole thing humming — landing in your inbox every Friday.

Free. One email a week. Unsubscribe anytime.

What's inside

Three sections. Five-minute read.

We sift Skift, Phocuswire, ShortTermRentalz, VRM Intel, AirDNA, operator podcasts, and the corners of LinkedIn worth listening to — so you don't have to.

  • Section 01

    The 5 Headlines

    What actually moved this week — across STR, boutique hotels, and the tech that runs them. One sentence each, links to dig deeper.

  • Section 02

    Pro Tip of the Week

    One tactical thing you can use Monday morning. Pulled from operators in the field, not consultants in slide decks.

  • Section 03

    Dream Weaving

    A beautiful listing, a guest experience worth stealing, or a design idea to file away for your next refresh.

A look inside

Issue 001 — a preview.

The Check-In · Friday, April 24, 2026

NYC's STR crackdown, AirDNA's bullish 2026, and the art of a memorable welcome.

The 5 Headlines

  • — NYC's enforcement office found 27% of "approved" STR listings are now operating illegally — mostly entire-home rentals or guest-cap violations.
  • — AirDNA's 2026 Outlook: best year to invest in STRs since 2021. Listing growth projected at 4.6% (vs. ~20% in '21–'22), occupancy easing just ~1%.
  • — VRNation officially launched its Pro Academy on April 22 — a peer-developed education platform offered to all members at no additional cost.
  • — PriceLabs shipped its 2026 Revenue Accelerator: 30+ features including a Market-Driven Base Price Helper that benchmarks against your local comp set.
  • — Airbnb's April 20 ToS update banned AI-generated damage evidence (after a $16K fabricated-AirCover case in NYC) and forced all pre-Feb accounts to re-accept terms or lose access.

Pro Tip — the 48-hour check-in note

Two days before arrival, send a short note that names one thing specific to their booking — the trail they asked about, the late checkout you confirmed. Generic pre-stay emails get ignored. Specific ones get screenshots. We've seen review rates jump double digits from this one change.

Dream Weaving — borrow one detail from their booking

The fastest way to WOW a guest isn't a bigger welcome basket — it's specificity. Pull one detail from their booking inquiry (the anniversary they mentioned, the kid's name, the trail they asked about) and put one thoughtful thing in the rental that addresses it. A small bottle of bubbles for the anniversary. A hand-drawn welcome sign with the kid's name on their bedroom door. A trail map left on the kitchen counter with two pencil notes from a local. Generic gestures get filed under "expected." Specific ones get screenshotted, shared, remembered — and rebooked.

Sources

Credit where it's due — and a doorway in if you want to dive deeper on any of the above.

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Who it's for

Built for the people actually doing the hosting.

Skift is great. It's also written by reporters. The Check-In is written by people who've stripped a bed at 11pm and answered the "is the hot tub working?" text on a Sunday.

  • Property managers running 5 doors or 500
  • Owners self-managing their place
  • Boutique hoteliers and innkeepers
  • Co-hosts and operations leads
  • PMS / hospitality-tech folks who want operator signal
  • Anyone curious about the business of hosting

Brought to you by

Ohana Vacations

We manage and broker short-term rental properties across Maine, Vermont, Oregon, and Costa Rica — where every guest is treated like family. The Check-In is our way of giving back to the operator community that taught us most of what we know.

Thinking about selling your STR business or handing the keys to a team that knows the work? That's us too — ohanavacations.com.