My dream would be to live in London, with my sister and her little family. For 39 of my 49 years, I've lived in Chicago, a medium-sized central Illinois city, and Pittsburgh. The other ten in a small town (12k pop) So I do understand the pros and cons of living big city/small town.
I'm now living permanently in that small town in central Illinois, and although kind of boring, it's good enough for me.
My two sisters and their families are here. We all help each other out. Traveling to see family is much more difficult when you get older. Plus taking time off work, the expense, etc.
We have a good hospital, and I live between four larger cities with great healthcare options. (Shout out to St. Francis Hospital in Peoria for literally saving my life 13 years ago)
There's not much shopping, but it's enough. Having limited options actually saves money because I can't do much "shopping as entertainment" LOL Walmart, Aldi, IGA, Dollar General, Dollar Tree, Big R, Gordmans.......we just lost our Kroger, so I'm sad about that
The larger cities near me have anything else you could want, and online shopping is a godsend.
There are several churches, and most are very involved with the community, and have several fun events throughout the year. I am not religious, but I do appreciate how sometimes churches can enhance a community.
We have THREE colleges. One community college (which has expanded its offerings to health care programs), one private 2-4 year, and one Christian 4 year.) I've lost count of the many universities and colleges within a one-hour drive from here.
I can get over 20 television stations with a good indoor antenna.
We have a nice library, with a lot of kids programs.
It's quiet. Crime is very, very low.
Property taxes are very high, as they are in Illinois, overall (there has been a large exodus of Illinoisans to Tennessee, LOL) I rent, and the landlord pays her taxes with my rent...........the property taxes on my 2-bed semi-detached with no garage is $1800/yr.
A good-paying full-time job is hard to come by. There are two prisons and a couple of factories. We have many nursing homes, assisted living homes, and developmentally disabled homes. I think we are expanding on that, because as the baby boomers get older, more homes will be needed.
You really need a car. There is one taxi that might show up. There is one bus that runs a few hours each weekday, and takes an hour to get across town, where driving takes five minutes. I don't know why they bother. You can reserve a shuttle bus to take you to out-of-town doctors appointments, $10. (Note that this might be covered by Medicare or other health insurance).
Some specialist doctors come here from the larger cities one or two days per week, because we don't have those doctors here. For me, it's my orthopedic, and ear-nose-throat. While this seems inconvenient, they never used to do this and you had to drive 30-60 minutes to the other cities.
Family and healthcare are the most important things, as everyone else here has said.
When considering places to live, include the benefits of cities within an hour's drive.
edited to ad: I'm also 2.5-3 hours from Chicago and St. Louis, with Amtrak to both. It's really nice to have HUGE cities close enough to day-trip to, so that's a bonus when looking for a place to live.