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The 5 Most Expensive Mistakes New STR Operators Make
Regulations, platform dependence, the wrong insurance, underpricing, and ignoring the real numbers — the five avoidable mistakes that cost new operators…
4 hrs ago
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J. Massey
How to Price Your STR: A Dynamic Pricing Primer
Setting a nightly rate once and leaving it is the costliest passive mistake in the business. The three levers, the right tool, and the 30-day rule.
Jun 23
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J. Massey
2
1
How to Scale From 1 to 10 STR Properties
The jump from 3 to 10 isn't a bigger version of what got you to 3 — it's a different business. The systems, hires, and capital plan that make it…
Jun 22
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J. Massey
Rental Arbitrage Was Never a Side Hustle
A $2,000 lease grossing $4,200 isn't a side gig — it's a business. Why the side-hustle story is the thing keeping most operators small.
Jun 21
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J. Massey
Invest Where Your Life Already Goes: The College-Town Housing Thesis
My daughter picked a college town. Then my investing filter kicked in. Why college towns beat vacation markets — and the four checks before you buy.
Jun 20
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J. Massey
1
4
You Don't Have a Hunger Problem. You Have a Gap Problem.
You understand the sequence but you're still not moving. The reason isn't knowledge — it's what you do with the distance between where you are and what…
Jun 19
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J. Massey
Your Property Isn't Hospitality. It's an Export Business.
The World Cup exposed it: you're not renting a room, you're exporting a guest's whole experience of your city. Operators who see it stop competing on…
Jun 18
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J. Massey
VA vs. Operations Lead: Why Most STR Operators Hire the Wrong One
A VA takes tasks off your plate. An ops lead removes you as the ceiling. Most operators hire them in the wrong order — and pay for it.
Jun 17
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J. Massey
1
The World Cup Didn't Create Opportunity. It Revealed the Demand You're Missing.
Booked demand is up 40%+ in host cities while asking rates doubled — and the real lesson is the year-round demand you can't see.
Jun 16
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J. Massey
1
World Cup 2026: Most Operators Priced With Pride, Not Math
Across 16 host cities, asking rates ran $497 a night while guests booked at $332. Here's what the booked data actually rewarded.
Jun 15
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J. Massey
The $2,300 That Meant Two Different Things
Same property. Same revenue. Thirty days apart, the number flipped from a win to a floor — and that flip found $400+ a month.
Jun 13
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J. Massey
596 North Flores Street Is Old Enough to Vote
I closed my first deal with a 398 credit score, three months before Lehman collapsed. Here's the only thing that deal was actually for.
Jun 12
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J. Massey
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