How to Choose Your First Market


October 21st, 2025
Read time: ~3 minutes
Hospitality is changing faster than we have ever seen. Each week, I share insights and strategies to help you navigate the future of hospitality marketing, revenue management and the demands of the Modern Traveler.
Let’s craft the future of this industry together.

Your first landscape resort or unique stay project lives or dies by one critical decision: location.

After developing over $50M in landscape resorts, I've learned that selecting the right market isn't just important—it's everything.

This week, I'm breaking down my 7-step framework for identifying the perfect market (and land) for your first hospitality project.

1. Proximity to Your Home Base

Your first project needs to be a maximum two-hour drive from your home base. This isn't a suggestion—it's a non-negotiable rule.

Distance kills involvement, and involvement determines success.

You need to be on-site constantly. Learning. Problem-solving. Adapting. Every single day. Your first project is as much about your education as it is about creating a remarkable guest experience.

2. Metropolitan Access: Where Can You Pull Demand From?

Your project needs to be within driving distance (1.5 hours) of a major metropolitan area.

Ideally, multiple metros feeding potential guests.

A property 3+ hours from the nearest city creates friction for guests who could easily choose a destination half the distance away in most cases.

Our Onera locations were chosen with this in mind. Both being less than 1.5 hours from Austin and San Antonio.

3. Food & Beverage Proximity

Restaurants, Main Street and grocery store access from your location is a huge factor.

If you're within 15 minutes of dining options, you can skip complex food and beverage operations altogether, as guests can easily access dining options.

But venture 30+ minutes from the nearest restaurant/ large store, and you'll need a strategic solution.

For your first project, consider these F&B approaches:

  • In-unit kitchens
  • Small commissary with essentials
  • Pre-packaged meal options

Pro tip: Avoid full-scale restaurants on your first project. The operational complexity isn't worth the headache and more than likely they will lose you money.

4. Existing Demand Drivers

Not all markets are created equal. The best locations come with built-in demand drivers that reduce your marketing burden.

In our Hill Country destinations (Fredericksburg and Wimberley, TX), we have natural advantages—vineyards, major events, hiking trails, swimming holes—creating a steady stream of potential guests that were coming long before we even opened.

When choosing markets without existing demand, you face two paths:

  1. "Make the Market" from scratch (requires exceptional marketing)
  2. Limit your unit count to maintain occupancy

Unknown markets demand extraordinary marketing as you're not just selling a stay, you're selling an entire destination.

Larger projects require substantial demand drivers, or you'll find yourself fighting an uphill battle to attract guests.

For your first project, choosing a market with an inherent guest draw is the best path forward.

5. Operational Hurdles for Remote Markets

Just as marketing challenges emerge in unknown markets, operational complexities can quickly transform your dream project into a logistical nightmare.

Remote locations introduce significant operational roadblocks:

  • Limited talent pools make hiring difficult
  • Fewer local vendors reduce guest experience options
  • Cleaning and logistics become exponentially more complex

Each challenge compounds the next.

Another reason to sway towards markets with existing demand.

6. Visual Appeal: Choosing The Actual Land

In today's digital landscape, visual appeal isn't optional—it's mandatory. Your property needs to make people stop scrolling on social media.

Dramatic desert canyons. Breathtaking waterfalls. Dreamy forest clearings. You need a landscape that tells a story.

Remember: People don't just book a stay anymore. They book an experience.

If you don’t feel the immediate urge to pull out your phone when you tour the land, it’s probably not “the one.”

7. Land Selection (The Details)

I learned the details of securing land the hard way after losing out on two perfect properties.

Here’s what to watch out for…

Zoning regulations and deed restrictions will make or break your project. Research thoroughly before falling in love with a property. Some seemingly perfect locations have hidden restrictions that can derail your entire vision.

Topography matters. Understand the terrain's potential for development. Steep slopes, rocky ground, or flood-prone areas can dramatically increase construction costs. Though often it’s worth it to build on these challenging properties, given their inherent beauty and wow-factor.

Speed wins. Turn on immediate notifications for when new properties hit the market and don’t drag your feet deciding.

Lastly, a contrarian take: Land cost is dramatically overblown.

In most markets, land represents just 10-15% of your total project cost for a landscape resort. Don't let minor price differences prevent you from securing the perfect location. The most expensive mistake isn't overpaying per acre—it's selecting the wrong market entirely.

Market selection is both an art and a science. The right location can make or break your hospitality venture, setting the stage for everything that follows.

Choose wisely. Your first project's success hinges on this critical decision.


Ready to have a team of experts running your marketing and revenue strategy?

At Oasi, we act as your outsourced Chief Marketing Officer and Chief Revenue Officer. Giving you executive-level leadership backed by a full team of specialists in content, social media, ads, email, SEO, and pricing strategy.

If you want to boost revenue and drive more direct bookings, we'd love to help.

Fill out an inquiry here and let’s explore how we can work together.

See you guys next week!

-Ben Wolff

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🎥 Check Out My Podcast with Steve Turk Diving into The Story Behind Baya, Our New Tropical Landscape Resort

🎥 Check Out My Episode on The Bigger Pockets STR Podcast on Redefining Luxury Hotels and Outperforming Traditional Hotel Models

🎥 Check Out My Podcast Episode on the Action Academy about Making Millions Through Direct Bookings

Ben Wolff
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Ben Wolff | The Unique Stays Guy

I build & manage unique hotels with the highest returns in hospitality. Learn how to grow your vision and go from commodity STRs to boutique hotels.

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