Billings Investor Case Study: Casey Gregersen, Wyohouses and 12 Closings Since 2023

Last reviewed and updated October 19, 2026

What does it look like when a Billings real estate investor and an agent work together over years, not one deal? For Casey Gregersen of Wyohouses, it started before I was licensed, with wholesale deals in Billings that mostly did not come together, and grew into 12 transactions where I was his listing agent plus the purchase of the Santa Fe Arms apartments, all since 2023.

I'm Gene Hauck, a Real Estate Broker and REALTOR® with The Morales Group at Engel & Völkers Billings. Residential investors are one of the two groups I focus on, and Casey is the client I point to when an investor asks, "Can I talk with someone who has bought and sold with you more than once?" This page tells that story with Casey's permission and in his words where they matter. Montana is a non-disclosure state, so no sale prices or deal terms appear here.

Who is Casey Gregersen?

Casey Gregersen is a real estate investor who buys, renovates and resells houses in Billings and holds rentals through Wyohouses. He also hosts the Rigs to Riches podcast, where he interviewed me about leaving the oilfield for real estate.

How did the relationship start?

Casey and I met before I had a real estate license. We were trying to make wholesale deals work in Billings, and most of them did not close. Once I was licensed with The Morales Group at Engel & Völkers Billings, I could write the offers, handle inspections and carry a deal through to closing myself, and that changed what we could do together.

Casey describes it this way:

"I've known Gene since before he even had his real estate license. We were trying to make wholesale deals work in Billings back then, and most of them just weren't coming together. But I always saw the potential in what we could build together. Once he got his license, he could write the offers, handle inspections, and take deals all the way to closing himself. That's when things really started clicking in Billings, and we were able to build something together that worked." Casey Gregersen, Wyohouses

What did the work look like on Casey's properties?

Across Casey's Billings properties, including homes on Custer Avenue, Moore Lane and Windmill Circle, three habits repeated.

Numbers before the purchase

Before Casey commits to a property, I run a comparable-sales check and an after-repair value estimate from Billings sales, so the buy decision rests on what similar renovated homes have actually sold for, not on hope.

Keep a deal alive when buyers fall away

The Custer Avenue renovation went under contract four times before it closed. Casey's team made most of the repairs along the way, and the final buyer chose to handle a few remaining items himself. Investor resales rarely close on the first contract. What matters is having a plan for the next buyer before the current one walks.

On Windmill Circle, a flip that otherwise went to plan, the sewer line needed to be replaced. Casey's team got it done and the sale closed. A sewer line is the kind of repair that can end a deal late in the process, so it is worth having a sewer scope done early on any older Billings property you plan to flip.

Solve the buyer's problem, not just the price

The Moore Lane property's zoning ruled out the conventional mortgage most buyers would use. Rather than wait for a cash buyer, Casey and I put together a creative structure, approved by a local bank, that gave a buyer a workable path to ownership.

What came out of it?

Since 2023 I have represented Casey on 12 transactions as his listing agent and on his purchase of the Santa Fe Arms apartments on Central Avenue in Billings. The relationship works because neither of us keeps score on any single deal. Casey brings properties, I bring the Billings market analysis and the transaction work, and we both come back for the next one.

Hear the story from Casey's podcast

Casey interviewed me on Rigs to Riches about the oilfield years, the first flip that went badly and how our partnership works.

What should a Billings investor take from this?

• Ask for repeat clients. One closing proves an agent can close. Repeat business from the same investor shows the agent's numbers held up.
• Expect analysis before the offer. Comparable sales and an after-repair value should come before you commit, not after.
• Look for problem-solving on the sale side. Failed contracts, late repairs and financing limits are where investor resales stall. Ask how your agent has handled each one.

For the full checklist, see how to choose an investor real estate agent in Billings. If you are deciding what to do with a property, Flip or Rental in Billings walks through how I make that call, and buying a duplex or multifamily property in Billings covers small apartment buildings.

Working on a Billings deal?

Start with the Billings real estate investing page. If you already have a property in mind, send me the address and I'll run the numbers with you.

Learn more about Casey's work at Wyohouses and caseygregersen.com.

This article is general information, not legal, tax, lending or investment advice. Past results with one client do not predict results on any other property.

Gene Hauck is a Real Estate Broker and REALTOR® with The Morales Group at Engel & Völkers Billings, 1921 1st Ave N, Billings, MT 59101. Montana license RRE-BRO-LIC-135399. 406-861-4844.