When buying a home, it is best to implement the five mile rule. While you may have to drive further to go to work assuming you are not working from home, all other amenities should be within five miles of your home; so doctor, hospital if possible, shopping, good restaurants and all other amenities. Some times people move further out to get better home prices and then have to wait often years for amenities to catch up. Driving more than five miles to get the goods and or services that you want gets old real quick. If you can help it, don't do it.
Most important, people facing retirement should NOT buy a home anywhere that does not have good medical services. This is becoming a big problem because the United States is facing a doctor shortage that will only get worse as many Baby Boomer doctors retire. As we get older, crap happens. The odds of having a chronic illness or accident from a fall increases dramatically once we get past 70. Being miles away from good medical services is just not a good idea.
Next, decide on the amenities that are important to you. If you enjoy performing arts, buy a home in a town or city that has a thriving performing arts scene within it. It does not have to be New York City caliber Broadway, but even second tier cities often have good performing arts venues. And then, there are restaurants. Obviously, big cities have more to choose from; but you don't need several hundred restaurants to choose from. As long as there are 10 or 15 good to great restaurants in town, that will be enough to satisfy your culinary needs.
The five mile rule is really a good idea related to quality of life. Especially as we get older, the last thing we should be doing is driving miles to enjoy life.