Welcome Back

 So, I've been back on Long Island 6 months now.

When I returned to Florida approximately a year ago, after spending the spring and summer of 2025 on Long Island, I continued searching for a job. It wasn’t successful. I had one interview that was particularly promising, and in the end, one of the owners spoke very frankly with me. She said she would love to have me on board as a property manager, but she asked me some thought-provoking questions.

Would I be happy with limited vacation time and the ability to move around the way I had become accustomed to? Would I be happy remaining in Florida if my husband never made the jump—which seemed more than likely? And would I be okay with being on-call and constantly available to tenants?

They were legitimate concerns once she laid them out for me.

I made some really hard decisions, and I talked them through in detail with friends who know me well. Ultimately, I decided to set up our Florida house as a vacation rental. And I mean REALLY decorate it and make it nice. Not just okay. Really nice.

That meant that any spare cash or available credit went into finishing the painting, packing away excess belongings, creating owner storage spaces, updating the outdoor furnishings, having my beloved patio seating set shipped down, and all of the other little things that would make the house feel special.

I had long conversations with my financial advisor, my girlfriends, my husband, and other family members. We celebrated Christmas and New Year’s in that house with all of my children, my mother-in-law, and cousins. And afterward, I packed everything away and focused on the job of becoming a rental owner.

I signed up with the same company that had wanted to hire me but, in a strange way, had given me the courage to make this decision instead. They became my property managers.

What they don’t really explain, though, is the fear that comes with wondering whether your house will ever actually be picked.

The community requires a 90-day minimum rental. When I started this endeavor, I said, “If it doesn’t rent well, we’ll sell.”

And that makes me sad, because I really do like the house. It would definitely serve my purpose as a getaway home and maybe, eventually, even a winter home—if only it weren’t in Florida.

Anyway, it has gotten a few hits through the property management company, but nothing has stuck. And now I’m thinking more and more about putting it on the market for real.

I want to make sure that, if we do sell, I can get the price we need so Jay and I can finally have something here in New York again. I work full-time in central Suffolk County, while he has been commuting into NYC for 35 years. He deserves a break.

I can part with most of the furnishings, except for a few pieces—some things that were gifts, things that have sentimental value. But even those need somewhere to go, and storing them until we have a place to settle will cost money.

It’s just so frustrating.

To be our age and feel like we’re starting over again because of decisions we made along the way is a hard feeling. We thought we were figuring things out. We thought we were making the best decisions we could with what we knew at the time.

And now I’m just trying to figure out what comes next.