The Hassles of Owning Homes in Two Different States—With Tips for How to Handle Them

I know this topic is a “champagne problem”, but for those of us nearing retirement, figuring out how and where to spend our time is a big issue. if you’re considering a part-time home in another state, it’s important to know the complexities that come with back-and-forth living.

The benefits of a second place are obvious—gorgeous weather, outdoor activities, beautiful scenery, new friendships, a change of pace, pickle ball. I spend half the year in vibrant Chicago and the other half in beautiful Bonita Springs, Florida while my husband comes and goes, depending on his work schedule. I’m super grateful to be able to live this way. I mean, look at my two beautiful views! But after four years, I’ve discovered some hassles (beyond the expense) about the “snowbird” lifestyle that I didn’t fully appreciate going in. I discuss them, along with tips to make things go more smoothly, below.

Mega Maintenance. This is such a dreary topic, but a biggie. Not only is it expensive to maintain two homes, it’s difficult to take care of them properly—especially if you’re 1200 miles away when something goes wrong. I had to deal with a bathroom faucet leaking into the unit below us in Chicago from a tennis court in Florida. All the chores and service appointments you dread are doubled—HVAC systems serviced, fire alarm batteries changed, humidifier filters changed—and so many more. Both our printers died mysterious deaths. If you have a yard, you have to arrange lawn care or snow removal. Developing a detailed master maintenance schedule with the contact numbers of key service people helps navigate this. So does hiring a home watch service or enlisting the help of a trusted friend. Stay vigilant with upkeep, but have a plan if something goes wrong. It will.

Danger-Danger. Living in two locations means you experience the risks of both environments as well as the benefits. In downtown Chicago we’ve had looting, rowdy mobs and carjackings. In Florida, we’ve suffered a devastating hurricane, flooding, and red tide. I avoid walking Phoebe alone at night for fear of encountering thugs in Chicago and rogue mating alligators in Florida. I’ve never been accosted in either place, but staying to well lit, well known areas and carrying a flashlight helps. Living through the unique troubles of both areas does broaden my perspective, which I think is a good thing.

Red/Blue State Weirdness. In Chicago the politics are generally liberal and urban concerns prevail. In my part of Florida, it’s quite the opposite. Moving from one idealogical bubble to another is disconcerting. I want to be open minded and respectful of other people’s views, while being true to my own. I make no secret of my support for the right to bodily autonomy and I proudly say gay! But politics are so awful and polarizing these days, I avoid engaging in arguments that are unlikely to change anyone’s mind and only create ill will. I’d rather focus on the things I share in common with a person and not make assumptions about his/her politics. If this would be difficult for you, choose your second home’s location carefully.

Document Dilemmas. It’s tough to make sure records and important paperwork are located where you need them. Tax time is especially challenging. I’ve learned from my Florida friends to create a file box that has the most essential documents (passports, wills, trusts, tax records, investment accounts, insurance policies, etc) and drive or ship it back and forth each season. (I’d say make copies, but our copier/printer is broken.) Our USPS mail forwarding is spotty and slow, so I try to pay all my bills online, ideally on autopay. I ask a family member to check our “away” mailbox occasionally, because there’s often something important in there.

Doctor Disconnects. Switching doctors is so hard. I still see my docs on the North Shore even though I left the suburbs for the city seven years ago. But if you’re going to spend months in a different state, you’ll need to line up some health care. Ask your local friends for their recommendations. After four winters in Florida, I’ve found a good dentist and dermatologist, but if I really get sick it’s still Urgent Care for me. Again, it’s important to have access to your medical records (either online or hard copy) for continuity and make sure you’re meticulous about check-ups when you’re in your base location. Right now I’m in Florida setting up my annual physical, gyno, mammogram, and eye exam appointments back in Chicago.

Lucky me to have found this beautiful squad of Florida friends!

Girlfriend Gaps. I feel so lucky that I’ve made a group of wonderful women friends here in Florida and I treasure my lifelong besties back in Chicago. But when I leave for months on end, it’s hard to stay in touch. My friends’ lives continue without me just fine—tennis games, weekend trips, concerts, celebrations, lending support in hard times. I’m inevitably missing out on something in one place or the other. Phone calls and texts help (Lisa and I share our Wordle scores each day) but there’s still a disconnect. During Covid, I pretty much stayed put, but I’m thinking I’ll do some “drop in” visits going forward so I don’t go so long without seeing my precious pals. And invite them to come visit me!

Less Travel. Some people reject the idea of a second home because they’d rather spend their time and money exploring the world. It’s true, I don’t travel as much since we bought our Florida condo, mostly because I don’t feel the need to get away. My back-and-forth lifestyle is engaging and relaxed, and the weather is always wonderful. I do worry, though—am I getting less adventurous? Something for me to ponder while sipping a Prosecco on the balcony.

Reentry Wobbles. My transition between places isn’t seamless. Whenever I arrive at my new destination I feel out of place for a couple weeks. Chicago seems hectic and crowded, packed with teens, trains and tourists. I have to walk Phoebe three blocks to get to real grass. On the flip side, when I get down to Florida it feels staid and snoozy. “What do I do here again?” I ask myself of my new location. I’ve learned the best way to combat feeling dislocated is to make lots of plans ahead of time, so I can connect right away with the people, places and activities I enjoy most. Chicago friends, I’ll be back soon, let’s book some concerts and Cubs games!

Concerts at Wrigley Field with dear friends! I love Chicago.

I hope this list has been helpful, but please let me know if there’s anything else you’re wondering about in the comments. And if you have two homes, I’d love to hear how you make the transitions work for you.

For more advice about becoming a successful snowbird, check out this story from Forbes.

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