Christian OsgoodCEO, Multifamily Strategy · CEO at Multifamily Strategy

Go BIG or go HOME

9 Nov 2025 · 1 min

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1:02

Christian Osgood bought a $4.5 million seller-financed resort he can stay at free by integrating it into his hospitality business. He argues that larger assets like resorts and apartment complexes are more profitable and easier to acquire than single-family rentals, which are labor-intensive and yield minimal returns.

Chapters

If you're gonna buy real estate, you got to go big, which means you probably need to buy beyond the money you have. I'm spending the weekend right now at my seller finance resort here. This is a $4.5 million property. I get to stay here for free whenever I want because I am the owner of the property. I bought it when I was dead broke. I actually bought this in my first year of buying real estate. This is what I learned. While I also bought the house next door, and both of them are on Airbnb, it is really, really hard to start a small business and make any money, and it's a ton of work. This came with the employees that are paid for by the resort, the White House, the expansion that we bought, the 4,000-square-foot house on the water. We were able to do that and add it into the existing business. But if you're trying to Airbnb and you're buying these little single-family houses trying to scale your business, what you find is a lot of people do a lot of work for very little actual profit. If you're going to do any business— multifamily, hospitality— do not do small single-family. You have to go big. It makes so much more money, it's so much more passive, and it turns out when it's bigger, it's actually easier to buy, not harder. So if you're considering a single-family investment, long-term or short-term rental, think a little bigger. Buy an apartment complex, buy an entire resort. You'll be glad you did.