If you’ve been following this blog for a while, you know I harp on one thing over and over: treat your short-term rental (STR) like a business—because it is one. It doesn’t matter if you’re self-managing or hiring a property…
Understanding Risk: If You’re Taking It, You Better Be Paid for It Risk in real estate investing isn’t inherently bad—it’s just something you need to be fairly compensated for. If you take on risk without understanding it, you’re gambling, not…
AI is Eating the World—And STRs Are Next I’m bullish on AI. I think it will disrupt everything. Some people think this is overblown. I think those people will look back in five years and feel like the people in…
The Feast or Famine of Seasonality Every market has a rhythm. Some move like a metronome, steady all year. Others resemble a Wall Street rollercoaster—feast in peak months, famine in the off-season. If you don’t adapt your pricing strategy to…
Let’s talk money—more specifically, how to maximize it in your short-term rental. No fluff, no theories. Just a real-world case study of how we took a neglected unit in one of Oahu’s most competitive vacation rental buildings, applied a few…
Why This Matters (And Why You Should Care) My name is Braedon, I’m a co-founder of Island Stays Hawaii, a property management group specializing in short- and mid-term rentals in one of the most competitive vacation rental markets in the…
Welcome to Paradise, Now Let’s Talk Numbers Ah, Oahu. White sand beaches, swaying palm trees, and the sound of the ocean at your doorstep. It’s the dream, right? Well, if you want to turn that dream into a cash-flowing short-term…
If you’re familiar with the Oahu short-term rental (STR) market, you know the inventory is fairly homogenous—high-rise condos, typically 1-2 bedrooms. Unlike the mainland, where you can throw in a hot tub and a pickleball court and call it a…
The Bar is Rising. Are You Keeping Up? Short-term rentals (STRs) used to be a wild west—anyone with an extra room, a mattress, and a WiFi password could rake in cash. But the industry is professionalizing, fast. Guests expect more.…
In case you’ve been living under a rock—or worse, in an overpriced, underwhelming Airbnb—the gold rush in short-term rentals is over. That period when you could throw an air mattress in a spare room, list it for $200 a night,…