My Friends and I Bought a Condo in Hawaii

My friends and I have individual condos in Vegas, an island in eastern Canada, and a flat in Budapest. It’s not the same group for each property, but there’s a lot of overlap. I realized that none of our places are ideal for winter, though Budapest does have its charm, so I started thinking about tropical places that would be good for quick escapes from winter (it even gets cold in Vegas).

When buying these shared places, cost is a major factor. The property has to be cheap enough that everyone can afford it without needing to go there constantly to make it worth it, and also so that no one ever needs to sell to free up cash. Every property we’ve ever bought has been under $100,000. Those factors eliminated a lot of popular winter spots.

My first choice was San Juan, Puerto Rico. I had been once and thought that it was a really cool city with a mix of good beaches, good healthy food, and a nice downtown area. I sent out an email to my usual group of friends, got a group together, and booked a cruise that ended in San Juan so that I could go check it out.

In the meantime the hurricane hit, but I was undeterred. I figured that I could see which buildings could survive a hurricane and if I still liked the city at its worst, it would only get better from there. Plus, maybe some people would want to move to a non-hurricane-prone city and prices would be good.

But when I got there I didn’t like it as much as I had remembered. Or, rather, the area I really liked was smaller than I had remembered it being, and the surrounding areas weren’t that great. It didn’t feel like a home run, and prices were fairly high for even a one-bedroom. I lost motivation and decided to look elsewhere.

When I was sixteen I had my first girlfriend ever, Allison. One summer she came with me and my family to Boston, and I got to go with her and her family to the Big Island of Hawaii. I learned how to scuba dive, drank a lot of passion-orange-guava (POG) juice, and had an awesome time with her and her family. We spent most of our time in Hilo, on the east coast, and a bit of time in Kona, on the west coast.

I remembered the Big Island being really great, so I checked out properties and found some that seemed impossibly cheap at around $50,000 each. I called a real estate agent and found out that they truly were impossibly cheap. In Hawaii you often own the structure but pay a lease fee every month for the land. The properties I wanted had the lease coming to term in seven years, which meant that you could pay approximately $50,000 extra to own the land outright, or get your condo confiscated when the lease ran out. Still, $100,000 for a two-bedroom condo in Hawaii seemed reasonable.

I flew down to check out the property, but hotels were so expensive and my schedule was so packed that I decided to take a red-eye and stay for only one night. It rained the whole time, but I drove around the neighborhood and it seemed much better than I expected. The location was absolutely ideal, just a ten minute walk from the restaurants downtown and another 3-4 to the ocean. I had been concerned that maybe my memories of Hilo were a bit rose tinted because I went there with my first girlfriend, but I found it to be even better than I had remembered.

I sent an email to friends and had enough interest to make it happen. A perfect unit came up a couple weeks later, they miraculously accepted my first offer (and also gave me $500 back because they didn’t want to fix a $20 valve), and we owned a place in Hawaii!

The more time I spend in Hilo, the more I love it. I’ve been to Oahu, Maui, and the big island, and I think Hilo is the best city amongst all of them (though Honolulu has some really cool stuff too). The people are extremely friendly, there’s tons of healthy food, and it doesn’t feel touristy at all. Instead of a few huge sweeping white sand beaches there are dozens of smaller beaches, each one unique. Some have black sand, others white. Lots of them have areas with short bermuda grass. Some have lagoons, some have lava rocks to climb around on. Sea turtles are everywhere.

The downtown is full of quaint 100-year-old bulidings and is right next to the ocean. Everything is walkable and it’s also easy to park. Outside of Hilo there are tons of parks, the two mountains, and all sorts of other nature to enjoy. It’s also nice to have Kona only 90 minutes away to have another option for good flight deals (and a much better craigslist inventory).

There’s even a legitimate teahouse in Hilo and at least two tea farms on the island, which I haven’t visited yet.

Amazon will ship to Hawaii, as will many other online stores. I had two queen-on-queen bunk beds waiting for us along with four mattresses. I had a guy selling a minivan pick me up from the airport, and I bought it and drove home, so even after being here for only two days it feels like home.

I imagine that we’ll use the Hilo condo for short trips with friends, scuba trips, family trips, and a home base to work from when weather elsewhere gets cold. We split this one only six ways and have four big beds, so it’s unlikely that an owner would even come here and not have a bed waiting for them.

My friends and I who do these shared real estate deals always wonder out loud why more people don’t do them. So far the benefit we’ve gotten out of each has been enormous, especially in terms of great shared experiences amongst us friends. Though I wrote it before buying this Hawaii place, you can read a lot more about how I do these deals in Forever Nomad.



Photo is a cool little beach across Hilo Bay






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