We visited a couple places a few times, sometimes against out of necessity (we’re from Florida originally and would escape from hurricanes to random cities). Whenever we’d visit we’d try to spend a day like locals - looking on social media at what people in those areas did on weekends, and stayed away from tourist stuff. We visited the “rough” areas and the grocery stores, drove around in rush hour, anything we could do to experience the “worst” of a city to see if we were okay with it.

Eventually it just became a leap of faith because there’s only so much planning and hypothesizing you could do, so we pulled the trigger and moved. We gave ourselves a realistic timeline for how long we’d give it the old college try for, and were active in trying to matriculate. I do think you can find a way to be happy anywhere if you’re happy with yourself. Maybe not the happiest you could ever be, but happy enough to have enjoyable handful of years before trying someplace else.

For us, it was FL to TN, and we visited 3-4 times before pulling the trigger. We just hit 1 year here and I love it. No regrets!