I think a lot of the issue is just what you're used to doing. To a certain extent, you accept what you're stuck with and deal with it. "To a man with only a hammer, all the world looks like a nail", etc.

Fixed-gear fans will tell you it's the greatest thing since sliced bread. But historically, fixed-gear bikes were the original type, and coasting bikes and mult-speed bikes were the later development that overtook them. So evidently, the millions and millions of people riding fixed-gear bikes all those many years didn't feel like they were such a cool item back then, and happily upgraded when they could.

I rode a Worksman cruiser for a couple of years and put about 7,000 miles on it. And I was okay with it. But there were limitations, too. Group rides were out, as I couldn't keep up with most groups (those bikes are geared 42:21 or so, it's fairly low). There were a couple of rides I couldn't complete because I got too hot and too tired. I mostly avoided hilly routes. And when I got interested in riding farther, I changed up what I was doing.

To my way of thinking, winds would be a major reason NOT to ride a single-speed bike. That Worksman worked pretty good in the wind, because around 12 mph was a good pedaling cadence, and I could just crank into a wind. However, I was not able to ride 30 mph with a tailwind, which is something I can do on the current bike.