Maybe if we just throw ideas out there we can narrow down preferences as you shoot them down. I can think of lots of other things that would factor into my decision that you don’t mention.
So, in the spirit of throwing stuff out and seeing what sticks I’ll throw out three small towns that I’ve visited and loved – Northfield, MN, Kohler, WI, and Golden CO. What do you think of those ideas?
What size town are you thinking about? Small town can mean different things to different people. Less than 1,000? 5,000 to 10,000? Up to 25,000?
I’m not sure if this will help or be more complicated, but where are your kids settling down? Maybe you could look at areas within an easy direct flight of them or a 3 hour driving radius?
I looked up the three towns he mentioned and they were all about 20K.
In my experience, if you have no idea right now where you want to move to, just wait. Things happen. Maybe your kids will settle in more or less the same area, and that will drive your decision. You mention it’s just you – no spouse or partner, I assume – so maybe you’ll meet someone and want to be closer. Or maybe, just maybe, you’ll decide you like where you are just fine and either stay put or just downsize.
I’ll put together some more info to help out, so the thread doesn’t get cluttered with questions for me. But to the ones already asked -
The kids are nowhere near settling down - daughter is potentially starting a med-school path, in which case she won’t “settle down” for at least 8 years, and son is the type to “go where the job will take him”, and it’s the entertainment field so who knows where he’ll end up.
I don’t really think population is the determining factor for a small-town ‘feel’. I grew up in a town of 7k and lived for many years in a town of 30k… they both were tight-knit, with a walkable town center where you knew a lot of people. They had a local community band (which I played in), and various festivals throughout the year.
Basically the ‘real versions’ of what you see idealized in TV (think Gilmore Girls, Virgin River, most Hallmark movies, etc). NJ does have a lot like that, and I imagine a lot of the northeast does as well.
Unfortunately, I don’t have many living friends or relatives that are anywhere besides the places in NJ I’m already familiar with, so so far it’s been Googling something like “best small towns to live in” and stuff like that. Even beyond that - trying to blindly find nice places to rent is not easy - ever search for “luxury apartments in ” or something like that? every place calls itself a “luxury” apartment…
Anyway I’ll try and come up with some more criteria. Thanks!
I am loving city life but would strongly consider Northfield MN if I were looking for a small town. Kohler WI is lovely, too.
@Schadret - what sort of hobbies/activities do you enjoy (or would like to try)?
What’s wrong with where you are right now?
Honolulu has a small town feel, even though it’s a big city. Sone neighborhoods are walkable while others aren’t. Unfortunately, cost of living is quite high. Neighbor islands have even more small town feel.
That’s why I’d rent first. At the moment I’m a transient - my lease was up in NJ a few months ago (winter/seasonal rental on the beach in Margate), so now I am back in FL at my folks to help them recover from surgeries. Once they are mobile again (~2 months) I need to move somewhere. I have no issue renting for a few years in various places to try them out, then settling once I find a place a place I really click with.
Perhaps look at categories from a site like Niche.
I would consider your preferences concerning weather, city/suburb, demographics, etc.
For instance I live in the Midwest in a suburb of Chicago. We could relocate but are very happy where we currently live. We like 4 seasons, access to O’Hare for travel, proximity to Chicago for culture/sports/entertainment, Lake Michigan for water, etc.
Shadret - I’ve had some of the same thoughts.
At first I’d simplified my search by thinking I’d go where my 32 year old son lives (beautiful western state). But he also hasn’t finalized his permanent locale (although it very well could be where he is now).
So have forced myself to start some “from scratch” thinking about where I’d want to be.
As part of that research I’ve been listening to the “Retire There” podcast hosted by a couple who are looking for a retirement locale and interview many people who have moved various places for retirement. Super enlightening.
I’ve also thought a lot about weather. Do you like the heat? Hate the cold? Worried about the impact of climate change on more vulnerable locales?
Also politics (don’t mean to start anything!) - does it matter what the predominant political persuasion in the area is?
Also college towns - those have a lot of vibrancy and appeal - is that a factor?
Also healthcare and airports - are there both of these nearby to where you might consider? How important are those to you?
And type of nature - are you drawn to the mountains, beaches, something else?
For me I’d start with these categorizations first, rather than random towns. Although random towns might work too, lol! 
For us, we’d probably not consider any location not near family and/or friends. I admire those who are adventurous enough to do so. But I do joke that if we found the ideal place to live… we’d likely not be able to afford it.
One idea for OP could be to settle somewhere affordable within driving distance of the FL parents. Then take some vacations (with remote work extensions if you possible) in various areas/seasons.
I’d also want to be sure to be a major airport and excellent healthcare that is still accepting patients. Medical issues become increasingly important as we age. May want want to consider communities that have that have excellent resources for elders and interesting communities for 55+?
I second the healthcare and airport. The rural area H and I grew up in currently has no hospital (2 recently closed). It is about 1/2 hour drive to other small rural hospitals. Specialty care is a longer drive.
Airport is important even if you are not inclined to travel. Your kids will want to visit you and you want that to be convenient (ask me about having parents/in-laws who lived 2 hours from a major airport).
I would also think about public transportation and availability of Uber/Lyft especially as you age.
There are many towns in the Boston suburbs that, if you don’t mind winter, are like those towns in NJ that you mentioned (which I am familiar with as I live near them).You can find these towns along the commuter rail lines (just like in NJ). As Boston suburbs they have all the amenities mentioned - access to airport and great hospitals. I like to check out the local library websites/social media to get an idea of the community feel of a place (what kind of programs do they offer, who is attending, etc.)
There was a CC’er - female I think - that sort of when from city to city staying several months or so before moving on… she kept a home base where I think one of her college aged kids lived (trying to remember for sure) but she chose different areas - she may have actually been like house sitting - and could work wherever she landed.
I can’t remember her name! Her avatar was unique.
I think you may be referring to @compmom.
I grew up in Mountainside, so I know what you mean. We ended up moving from Tokyo to southern France a few months ago, but before deciding on France, we looked seriously at the idea of moving back to the US and we were more or less in the same position as you - we could have gone anywhere. I remember being very intrigued by Providence, Rhode Island. If you don’t mind the cold, Portland, Maine is another great place. They are both small cities, but they have more of a small-town feel. We lived in Los Angeles for a couple of years and loved it, so I also looked at places like West Hollywood that have a neighborhood vibe and are walkable to shops, etc. Growing up in Mountainside, where the only way to get anywhere was to have your parents drive you there, walkability is very important! Even here in France, it was a gating issue for me, and we ended up in a place where we can walk to our local shops, the bank, etc. in about ten minutes.)
I think I posted this upthread someplace. I would move to Columbus, Ohio but my husband is not on board with that idea. There are wonderful neighborhoods, and parks, somewhat milder winters, and tOSU is there which offers plenty to do in addition to what else is in the city.
The Clintonville area of Columbus has great homes, smaller but nice, and with much more modest prices than where we are in New England. Very walkable to places like restaurants, grocery, gyms, library, park, etc.