July 23, 2024
44 S Broadway, White Plains, New York, 10601

‘I have never had the freedom to just move anywhere’: I can move anywhere, but I don’t know where to go. How do I choose the perfect retirement spot?

Hi Moving Diaries,

Man, I feel so swamped trying to figure out where to retire. All my moves have always been because of family, school, or work. Now, I finally get to choose for myself, and it’s like being at a restaurant with way too many options!

I’m 55 and planning to retire in the next 4 or 5 years—sooner if my company hooks me up with a decent package. I’m single, never been married, and have no kids. Marriage isn’t really in the cards for me now.

Here’s a bit about me. Born in New York, I grew up in Connecticut and New Jersey. Went to college in Illinois and spent 25 years in the Chicago area (city and suburbs). 10 years ago, I moved to Sarasota, Florida for work. While a lot of folks retire here, it’s not 100% my thing. Beaches aren’t my jam, and I do like some changes in weather, which Sarasota lacks. Plus, it’s getting super crowded and overbuilt. Hurricane season? Total stress-fest. I was here for Irma and Ian—no house damage, but no power for 5 days sucked. My homeowner’s insurance has nearly quadrupled, and car insurance is crazy expensive too.

Real estate’s been kind to me here though. Bought a house in 2016 for $314k, sold it in 2022 for $600k. Moved my mom down here in 2021 after my dad passed, got her a nice place for $330k. She’s now in assisted living, and her place is home for me now. But it’s worth around $450-500k as the market’s dipped a bit. No mortgage, and property taxes are about $3400 a year—not too bad compared to Illinois. However, I’m stuck in a super restrictive homeowners association. I’m totally fine with an HOA, just not one that’s overly strict. I’m currently the treasurer, soon to be president, of the board here.

I’m not into living in a big metro area. Looking for a quaint, small city or town. An airport an hour or so away would be great. I dig dive bars, live music, trying out new restaurants, bird watching, casual biking, and chilling at home with my vinyl collection. A house surrounded by trees or with a cool view would be perfect, but still close enough to town for an Uber ride. Friendly neighborhood taverns are a must. Health care isn’t a big deal right now, but let’s be real—I haven’t led the healthiest lifestyle, so future needs do matter.

States on my radar: northern Georgia, northern Alabama, Arkansas, eastern Tennessee, western North Carolina, and western South Carolina. Haven’t really given Mississippi much thought. I’ve been to these states for work but mostly hit the big cities. Random spots popping up in my searches include Guntersville, Alabama; Brevard, North Carolina; Hendersonville, North Carolina; Murphy, North Carolina; Hot Springs, Arkansas; Eureka Springs, Arkansas; Blue Ridge, Georgia; Ellijay, Georgia, and a few more. Haven’t visited these places, so it’s just a hunch I might like them. Greenville, South Carolina is also on my list—been there many times, but it might be a bit too large. Being within a day’s drive to Chicago to catch up with friends would be cool, but not a deal-breaker. Definitely avoiding anything near a coast with hurricane potential. Need to narrow down these options, though, before I start visiting.

Politically, I lean conservative.

Ideally, I’d like to sell my house for $500k (who knows what it’ll be worth in 4 years) and buy a new place for around the same price. I’m okay spending a bit extra from savings if needed. Florida’s lack of state income tax is a plus, and I think Tennessee is the only state on my list with a similar setup. So, I’d prefer a place with favorable taxes and reasonable property/home/car insurance too.

Anxiously Seeking Advice
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