My parents have finally become snowbirds. When they both retired from the military we "retired" in CT. They were fortunate to purchase a home that appreciated
very well over the 22 years they lived in it. I believe it was just paid off at that point too. About 5 years before they sold it, they purchased a home in a water-side development in Beaufort SC and rented it out long-term to military down there. They were also given some family land elsewhere in CT and used the proceeds of selling the first house in CT to knock down the crumbling cottage there and rebuild a smaller home. This has become their summer home, and after renovating the SC house 2 years ago, they've finally also moved into it and reside there most of the winter.
After they retired from the military, (both officers, so yes retirement benefits are well-cushioned) they both kept working and did very well for themselves in their second careers. Both my parents came from very little, and never really spoiled us when we were younger. But they've made some sound investments over the years and honestly, my dad was very frugal

vacations only happened if we could stay at a Navy Lodge nearby and usually involved museums and battlegrounds. By the time I went to college, they could afford to foot that bill and I'll be forever grateful for that. My second brother got a free ride to the USNA so that helped a bit too, I believe they used that towards the SC house purchase lol. Other than paying for our secondary education, that's the only spoiling we had: we were all still expected to work, I have been since 14, pay for our own things, and we each bought all our own cars, insurance, etc.
I say all that, because a lot of planning and saving has happened over decades for them to make this happen, as well as a bit of good timing.
My mom has had a very hard time going between the two houses. She likes her stuff. She's more settled now, but she got a bit crazy and kept forgetting she's supposed to be downsizing and splitting. It also didn't help right before, she'd had to downsize/organize/sell/clean both her aunt's estate and her mother's. She's tired. They've collected a lot of nice stuff over their years of extensive travelling with the military. It can be a little knick-knack-y but she's happy. Neither of them have serious hobbies that require lots of equipment, though my mom is a great cook too with two fully OVERstocked kitchens that hardly get used now since its usually just them two. They've only just both RETIRED-retired this year so they're on another round of "what next"... They're talking about adding an RV but they both need to come to terms that my mother is not the RV type of woman she thinks she is

I'm begging them to borrow one and test it out first. I know how this will end.
I think they also have a few small regrets too with the snowbird lifestyle - only because of grandkids. It's hard enough for me to get away to visit one place, now I gotta find times to visit two, and during the right times. My nieces live nearby in CT so its hard on both sides when they're gone all winter. For now my mom still insists on going back north for one of the winter holidays just to see them. (They always stop by our place whenever they go back and forth, it's the perfect halfway point). My brothers are upset they are committing to the two houses thing, but it's their money. They've set themselves up for what happens when crap goes south, so I'm not worried. It sucks when I can't visit more often - that drive to SC is ****ing brutal with a small child...and going north in the summer? shew. "Connecticut in the Summer" is literally a VERB for the wealthy of NY/NJ. It can get real bad too. But they at least make a real effort to come here as much as they can too.
It's a LOT to consider. As a child, and particularly the eldest daughter of snowbirds, I selfishly wish they weren't.