What to consider before taking the second-home plunge

What to consider before taking the second-home plunge


The author realizes she will now be working for the rest of her life, but at least she’ll have a great view. (Courtesy of Marni Jameson)

The no-going-back moment is etched in my memory. After four months of looking at beach condos, of flirting with the idea of a buying a getaway that we could also rent out, we finally had an offer in play. My husband, DC, and I were standing in the kitchen when our realtor — we call him Saint Bob — called to say that the sellers had accepted it.

DC and I locked eyes. We mentally replayed all the discussions where we’d reasoned that this was the time, now that the kids were on their own, and while we were both still working. We’d rather have tried and been sorry, than never tried and wondered.

I nodded. DC told Saint Bob to send the contract.

Never mind that this was the first time in my adult, self-supporting life that I felt financially under control. I needed to mess that up.

Saint Bob had taken us to see more than a dozen condos and sent links to many more to view online. Some were nice, but lacked an ocean view. Some had the view, but the complex was rundown. Some needed too much work. Some were too small. Some were too dark. One we liked was about to undergo a two-year construction project that would involve boarding up all the windows. Another was in a complex that discouraged renters. Although buying a second home that you don’t have to rent out to offset the costs is a lovely luxury, we’re not those people.

Discouraged, we told Saint Bob we were taking a break. He understood and assured us that even if we never bought a place, he had enjoyed getting to know us. Getting to know us? Sheesh! By this time, he knew our shoe sizes. He also assured us that he did this job because he loved it not because he had to, which was good to know since by this point, if we ever did buy a place, his commission would come out to about fifty cents an hour.

A couple months later, we noticed that a few new places had come on the market. I caved and decided to go look. One. Last. Time.

Saint Bob made three appointments. The first two places were so-so. Then I walked into condo number three. Until then, I had been trying to talk myself into every place I saw. This one I had to talk myself out of.

“Uh-oh. This could work,” I told DC. The place had a killer ocean view, came fully furnished, had an impressive rental history, and the seller was motivated.

And that is how we ended up standing in the kitchen telling Saint Bob to send the contract. The journey has begun.

If you’re thinking about taking the plunge into second homeownership — not that I’m recommending this foolhardy move for anyone — here’s what to consider:

Affordability: How to afford this was a big question for us. After consulting with our financial advisors, we got some confidence that we could swing it, especially if we offset the carrying costs (including taxes, insurance, HOA dues and utilities) by offering the property as a rental.

Convenience: Many people choose second homes out of state and spend half the year in one place and half in another. That’s fine; however, if you want a weekend getaway, choose a place that’s easy to get to. Our place is an hour’s drive.

Renovations: Know how much time, money and energy you are willing to spend to fix a place up. Do you want a fixer or turnkey? I wanted something livable that I could cosmetically improve over time.

Lifestyle: If you’re still working and can work remotely, look for a place that can support that. You might only need Wi-Fi and a desk. If you want family and friends to visit, get a place that has room for visitors. Can your pet come? Are you close to good restaurants? These were important factors for us.


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