DON'T SELL YOUR STR! Adjust Your Systems...

[Dan Gandee]

Lately, I’ve seen a wave of short-term rental owners selling off properties that, in my professional opinion, should be performing well. These are homes in solid markets, with great layouts and real potential — yet they’re being put up for sale. Why? Because the owners are frustrated, burned out, and convinced the asset “just isn’t working.”

But here’s the truth: it’s not the property that’s broken. It’s the approach.

After working with investors from all over the country, including those who own $1, $5, $10, $15 Million Portfolios (of STR's, MTR's, LTR's) I felt it was necessary to pull from those experiences and share what STR operational playbook - Because after closing over $100M+ in transactions on the West Coast, I saw a blaring problem with short-term rental investors — and it's not the one you think.

It’s not interest rates. It’s not regulations. It’s not even market saturation.

The real problem is that most STR investors don't actually understand the asset they bought. They underwrite like landlords but operate like hobbyists. They confuse ‘owning a property' with ‘building a business.'

Here’s the truth no one wants to admit: you didn’t just buy a house with a lockbox. You bought a micro-hospitality company that requires brand positioning, marketing funnels, client experience design, systems architecture, and cash flow management. And the gap between those who treat it that way — and those who don’t — is where the bloodbath is happening.

That’s why I’m seeing incredible STRs being dumped on the market by frustrated owners. They’re walking away from profitable assets, not because the property failed, but because they never built the operating model to make it work. And unless this mindset shifts, more investors are going to keep repeating the same mistake.

Here's what some of my top clients and colleagues are focusing on:

1. Curb Appeal & First Impressions

In STR, the thumbnail photo is your storefront. If it doesn’t stop someone mid-scroll, you don’t even get a chance at conversion. Operators systematize first impressions by:

• Design Strategy: Hire a short-term rental interior designer (not just a stager) who understands flow, photogenic layouts, and Instagrammable moments.
• Photography Package: Invest in professional HDR photography + lifestyle shots (guests using the firepit, coffee mugs on the deck, etc.).
• Exterior Systems: Seasonal landscaping contracts, pressure washing schedules, and lighting plans to ensure the home is always photo-ready.
• Listing Optimization: A/B test lead photos quarterly (e.g., pool shot vs. firepit shot) and measure CTR against competitors in your market.

System: Quarterly Design & Photo Audit Checklist — every 90 days, review your top 5 competitor listings and update your lead photo, titles, and descriptions to stay visually competitive.

2. Marketing Beyond Airbnb/VRBO

If Airbnb disappeared tomorrow, could your STR still survive? Operators don't gamble on algorithms; they own their marketing funnel.

• Direct Booking Site: Build a branded booking website (Hostfully, OwnerRez, or custom WordPress) that integrates with a PMS.
• Paid Media: Run Google PPC ads targeting “[Market] Vacation Rental” + retarget visitors with Facebook/Instagram ads.
• Video Funnels: Create short-form video tours on TikTok, Instagram Reels, and YouTube Shorts that link directly to your booking site.
• Email/SMS Capture: Collect guest emails at booking and automate a nurture sequence with discounts for direct re-bookings.

System: STR Marketing Flywheel — Drive traffic → Capture leads → Retarget past guests → Convert to direct bookings → Build repeat stay database.

3. Client Experience is Everything

In hospitality, the moment of truth is how your guest feels. STR operators build intentional experiences:

• Onboarding Journey: Automated, branded pre-arrival emails with check-in instructions, local recommendations, and FAQs.
• Tech-Enabled Check-In: Smart locks with unique codes, timed to activate only during the stay. No fumbling with key boxes.
• Hospitality Touchpoints: A welcome basket (local coffee, wine, snacks), handwritten card, and curated local guidebook.
• Service Design: Contract cleaning crews with a 24-hour turnover guarantee and post-clean photo verification system.

System: Guest Experience SOP — Document the 10 “moments of delight” (arrival, first impression, first morning coffee, etc.) and make them repeatable through checklists and automation.

4. Review Capture & Reputation Management

Reviews are the currency of STR. Operators don't "hope" for reviews — they engineer them.

• Automated Review Requests: PMS-integrated sequences that ask for feedback 24 hours after checkout.
• Guest Support Follow-Up: A mid-stay text asking “Is everything perfect so far?” → resolves issues before they turn into 4-star reviews.
• Social Proof Capture: Encourage guests to tag your property’s IG handle for organic visibility.
• Reputation Dashboard: Monitor reviews across Airbnb, VRBO, Google, and direct site for consistency.

System: 5-Star Review Engine — Pre-stay expectation setting → Mid-stay check-in → Automated post-stay request → Follow-up with direct re-booking offer.

5. Proactive vs. Reactive Problem-Solving

Operators know problems are inevitable — so they design response systems in advance.

• Maintenance Matrix: Document common issues (WiFi reset, HVAC troubleshooting, breaker panel locations) with photo guides stored in a digital binder accessible to staff/guests.
• On-Call Vendors: Build a bench of reliable local contractors (plumber, electrician, cleaner, handyman) with pre-negotiated response times.
• Tech Monitoring: Use smart sensors for noise, water leaks, and thermostats to prevent issues before they spiral.
• Communication SOPs: Response time targets (under 5 minutes for urgent issues, under 30 minutes for minor concerns).

System: Crisis Playbook Binder — a digital + physical binder with scripts, vendor contacts, and SOPs for every common guest problem.

6. Underwriting & Financial Discipline

Many STR owners bought emotionally — operators run models.

• Cash Flow Model: Build underwriting that includes all real costs (cleaning fees, utilities, management %, CapEx reserves, and realistic vacancy).
• Dynamic Pricing Software: Beyond Pricing, PriceLabs, or Wheelhouse to maximize ADR and occupancy.
• 12-Month P&L Tracking: Monthly financial reviews comparing projected vs. actuals.
• Stress Testing: Underwrite for worst-case scenarios (20% occupancy drop, ADR compression, regulatory tax hits).

System: Quarterly Financial Review SOP — Reconcile P&L, re-forecast cash flow, adjust pricing, and reset CapEx reserves every 90 days.

7. Location, Location, Location

No system can save a bad market. Operators apply discipline upfront:

• Demand Data: Use AirDNA, STR Insights, and local tourism reports before buying.
• Regulatory Scan: Research STR ordinances, permitting requirements, and enforcement history.
• Market Drivers: Prioritize locations with multiple demand anchors (beaches + convention centers, national parks + breweries).
• Seasonality Planning: Build cash reserves to cover off-season gaps or pivot into mid-term rentals.

System: Location Scorecard — A 10-point checklist grading regulations, demand diversity, seasonality, tourism growth, and nightly rate comps before acquisition.

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Last call...Here’s the reality: a handful of bad guest experiences should not determine the fate of your investment. If you walk away after one rough season or a few difficult reviews, you’re letting temporary pain blind you to long-term gain.

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You didn’t get into this business for a quick dopamine hit. You got in for the long haul. Yet too many owners are taking the next off-ramp the moment the road gets bumpy.

Short-term rentals aren’t passive assets. They’re businesses. And when you treat them like businesses — with systems, strategy, and hospitality at the core — they become some of the strongest performing assets in real estate.

If you're an STR owner feeling overwhelmed or considering selling, I'd challenge you to pause. Take a step back. Look at the bigger picture.

You may not need to exit — you may just need the right playbook.

But if your livelihood is on the line, then do what you need to do to liquidate and recover. 

—
Dan Gandee

[Jon Martin]

Quote from @John Underwood:

Some of these people could have bought poorly meaning they overpaid for what they got.

It's not a one size fits all situation.

That, or you understand the game better and realize you can redeploy the equity in a better way. Doing that now with the first property I bought.