Do I dare?

I've been small town shopping. Granted, my shopping has been limited to online looks and research, but I've found out a lot. 

Small towns are great to live in. Where to live in that small town is another whole story. Usually the "historic district" can be translated as once thriving, now the town's big-house slums. "Picturesque" homes usually mean huge price tags because the surrounding land which makes them picturesque is off-the-charts expensive. 

If you're elderly, you had better have lived there your whole life. That way you have some sort of support network around you in the form of neighbors you know (and who either adore you or fear you). When groceries are needed during bad weather, or your washing machine makes a grinding noise that echoes in your dreams, there is someone to help. If you slide in, older and new to the area, you'd better be self-sufficient for a while. Those thin lips and eyes cut to the sides as you walk by mean just what they look like - suspicion of anything new. 

I've limited my window shopping to towns that at least have a chain grocery inside the town limits. Considering I dread a five minute drive to Kroger now, a 30 minute drive to a grocery may force some rather odd meals until the spirit moves me to make the trip. Think a can of baked beans poured on a tortilla with pickled beets as a side dish. 

I have some possibilities, but I still wonder - do I dare dream of a cottage in an area that is more touristy than functional at my age? I really wish my age wasn't a factor. Then, there's can I afford to live in small town America - the best small homes, many beaten to the ground by generations of dwindling family or renters, have been sold to investors, torn down, and replaced with big city style wonders with hefty price tags. 

Have any of you successfully made the shift - without being a retirement fund baron(ess) of majestic means? What considerations did you have? What have you discovered? I need some eye-witnesses!