Sure, go move to a town like that. You’ll figure out pretty damn quick that “quaint” isn’t nearly as nice as you think it is.
I live in a town which is about half and half. Population of ~20K. On one side, we have a smattering of the basic box stores. The other side of town is the older, quaint district. I’d call it historic, but it’s not quite there yet - it’s still enough of a working downtown (as opposed to ALL gift shops and fudgeries) that “historic” doesn’t quite fit.
I’m in the largest town within about 150 miles (Green Bay, WI is the next largest, a little over 3 hours away), and am surrounded by many, many small towns that perfectly fit your criteria. They’re cute, there’s no McDonald’s or Wal-Marts, and they’re fun to visit. Live there? Hell no.
Let me tell you about life in the town I live in. We have a Wal-Mart, a Target, and a small mall, complete with a couple department stores. Before living here, I lived in and around Boulder, CO, so I have a good amount of experience living in a large metropolitan area as well (Boulder is 40 miles from Denver).
Shopping wise, I’m very limited. Sure, I can get the basics, but what if I want more than the basics? I recently took a business trip. I had a hell of a time finding stylish clothes, even with two department stores to pick from. Much of the clothing is geared toward senior citizens or very casual. Not many people 'round here need the kinds of clothes I’d like to wear to a conference. I managed to piece a couple outfits together, but it was difficult.
Books? There’s a decent used bookstore in town, but if you’re looking for selection, it doesn’t exist. Want to go browse for, say, travel guides? There might be 10 guides at one store in town. Want a specific book that’s not on the current bestseller list? Chances are you’ll order it.
Groceries? I can get the basics, but I’m a fairly decent cook (have to be, there’s not too many good restaurants here) and there are many ingredients I can’t get. The selection of fresh seafood (other than the lake trout and whitefish caught locally) was nil - I mean, NOTHING, other than a few tired frozen things - until the Wal-Mart expanded into a Super Wal-Mart and put in a fish counter. Asian food? I got what’s in the “Oriental” section of the local supermarket. Beer/Wine? There’s some decent small liquor stores, but nowhere near the selection that even a mid-size store in a larger area carries. When I’m tired of the 5-6 brands of “premium” beer the local store carries, I’m out of luck. Mr. Athena and I drink a good amount of champagne. There’s 5 brands in town. We get tired of them, quickly.
Misc items: Mr. Athena recently wanted a headset for his new cell phone. Can’t buy it in town, we’ve tried every phone store there is. When the battery in my car died (a BMW, no dealer within 150 miles) I had to order one. Mr. Athena needed a leather jacket to wear while motorcycling. Other than the incredibly overpriced, logo-emblazoned ones sold at the Harley store, there were none. Furniture? Anything other than the lowend crap, you order it and wait 12 weeks.
Restaurants: Good luck. There’s one decent place in town that serves basic, but well-prepared food. We have a few Chinese restaurants (there were none here when I was growing up), but they’re nothing special. No Mexican food at all, unless you count Taco Bell. No decent Italian, not even an Olive Garden. Japanese? Yeah right. A good high end place to go for special occasions? Nothing. Price-wise, the most expensive place in town is Red Lobster. Unfortunately, it’s got some of the most interesting food as well. Yes, that’s right - Red Lobster serves the most innovative meal in the town, unless you count the food I cook at home.
Despite all that, I do love living here. It’s a beautiful area, and my family is here. Could I have lived here pre-Internet? I highly doubt it. We rely heavily on the Internet for news, culture, and shopping. I would truly feel isolated here without being able to browse at Amazon, read news online, and access the SDMB. We take trips at least a couple times a year to larger cities to shop for the stuff we want to buy in person.
If the town were any smaller - ie, like the ones the OP describes - they’d be highly unlivable. Bitch all you want about Wal-Mart, it brings stuff to small towns that is simply unavailable anywhere else, including the cute lil’ general stores people think are so great. My local used bookstore is nifty, but I’d kill for a Barnes & Noble or Borders to move in. An Olive Garden would be a step above the local restaurants - really, most of them survive only because people here don’t know any better. Trust me, they aren’t gems of great homestyle cooking. They serve cheap food badly prepared. The chains and box stores are popular for a reason.