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“We couldn't be happier.” -- Bonnie and Jamie Wilkes enjoy the waters of Sarasota, where they bought a second home 34 years ago as a getaway from Chicago. Today they’re back to owning one home -- in Sarasota -- where they’ve chosen to retire. Photo courtesy of Kim Gourieux.
“We couldn’t be happier.” — Bonnie and Jamie Wilkes enjoy the waters of Sarasota, where they bought a second home 34 years ago as a getaway from Chicago. Today they’re back to owning one home — in Sarasota — where they’ve chosen to retire. Photo courtesy of Kim Gourieux.
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Is owning a second home all it’s cracked up to be? That’s the question I cast to my experience-wizened readers. And their resounding answer? A definitive sometimes.

Over the last two weeks in this column I’ve shared, in a general sense, the pluses and minuses of the second home. This week, I am giving the reins over to my readers, who have shared their first-hand knowledge of second-home ownership. Here are their lessons from the trenches, beaches, mountains and golf communities:

“Just think!”

“There we were, stretched out on the beach — in January!” begins Bonnie Wilkes, explaining how she and her husband, then Chicago residents, came to own a second home in Sarasota, Fla. “The temperature was in the mid-80s. Wow! We thought — just think if we could have this all the time!  We should buy a second home here.”

And they did. That was 34 years ago. “Never again did we feel that same level of relaxation while on vacation at that same beach,” she continued. “Some days we didn’t even make it to the beach because we were waiting for the refrigerator repair guy. Instead of strolling the gift shops in the village, we were at a big box store looking for a TV for the guestroom.”

A second home is just that — a second home, Wilkes said, “with all the responsibilities any home requires, compounded by the fact that your time to fulfill those responsibilities is your vacation time.”

But the Wilkes’ story doesn’t end there. They retired 10 years ago, sold the Sarasota condo and their Chicago home, and bought a larger place — in Sarasota — where they now live permanently.

“We couldn’t be happier.”

Renting beats owning.

“We’ve rented the second home and owned the second home,” said Claudia Latona, of Pittsburgh. “Yes, it’s nice to be surrounded by your own things, but owning a second place amounts to an expensive and demanding hobby. It’s much more relaxing to rent.”

Timing is everything.

Five years ago, Carol and Tom Gordon, of San Anselmo, Calif., bought a cottage on Lake Erie, where Carol Gordon went every summer while growing up. “I wanted it as a way to stake my claim in the east,” she wrote.  Now they are considering whether it’s worth keeping until they retire and can actually spend enough time there to justify the cost.

Gordon feels obligated to vacation there; however, getting there isn’t easy with their active older children. “So we think of selling. But not yet.  It’s too beautiful of a spot.  Sigh.”

What would she do differently? “We probably bought our second home too early, given our active family and the distance from California to New York. We would have been better off buying a closer place, or not purchasing a second home until our children were on their own.”

Location, location, location.

Waiting till the kids were grown made a second-home investment pay off for Jane Gold, of Saratoga, Calif. After their three children were out of the house, she and her husband bought a second home in Lake Tahoe.

“Our family always vacationed there, and we have fond memories of those times.” Five years ago, they bought a house close to the lake and just a four-and-a-half-hour by car from their main home, so they can take their dogs. “We don’t regret buying one bit.”

Familiarity breeds success.

Karen Shelby, of Decatur, Ill., and her husband, who are retired, paid cash for a townhome by the beach in Fort Myers, Fla., a year and a half ago. “We love it,” she said.

She attributes their success to scouting the area thoroughly to find the right part of town, and setting a price limit. “We stuck to our guns. We were tempted to get more house for our money, but opted for a better neighborhood.”

Now, by renting their townhome out January through March, they make enough to cover their carrying costs for the year.

Bottom line proves bittersweet.

Laurie Akin and her husband, both teachers, bought a condo 12 years ago on Siesta Beach, Fla., only 20 minutes away from their real-life house. When they weren’t enjoying the beach house, they rented it out.

However, last year when they retired, they did the math and realized they simply could not continue owning two households. Saying good-bye was bittersweet, said Akin, who savors the good times they had with family and friends, but doesn’t miss the “huge” responsibility.

“The romance of a second place is undeniable. But those magical moments must be balanced with the knowledge that real estate does not always go up. We took a loss when we had to sell what we imagined would be a good retirement investment. We are glad we did it, yet we are also glad we are out from under it.”

Costs accrue.

“All the costs of a second home increase over time,” writes Estelle Stetz-Marcus, who moved to Orlando from Massachusetts, and keeps her former home as her second home. Appliances need replacing, utility costs inch up, property taxes rise. “You have to balance the joy a second home gives you (and seeing her grandkids there is a big motivation) versus the costs that accrue and accrue and accrue. After a certain age you just want life to be a little less complicated.”

Freedom rings.

Ann Rosenwald, of Colorado, had a second home in Virginia Beach for 10 years. “We did have amazing family times there,” she admits. But now that they’ve sold the getaway, they have spent what they used to devote to their second home on traveling the world. “We’ve been to wonderful places we wouldn’t have experienced if we’d still had our beach house.”

Rosenwald sums up our readers’ advice well: “If a second home is stretching you, and making you feel you have to vacation there, it can be an anchor around your neck. But if having the vacation home doesn’t stop you from traveling to other places, then go for it!”

Join me next week when a financial planner shares a checklist to help you decide whether a second home is right for you.