I don't ride in winds above 20 mph. Although I *have* ridden in winds gusting up to about 40 mph, it's dangerous and not necessary. We don't routinely have winds that strong. I guess I'm not a big risk taker? When I was commuting, high winds certainly would have stopped me.
That said, I don't ride in the rain. Sure, I've been caught in the rain, and I don't like it, especially on my road bike. The first bad crash I had was descending a mountain road in Vermont, in the rain. And the first two days of my tour in the Czech Republic was in a cold rain. Nothing I could do about that. I have done errands on my hybrid in a light drizzle/rain and with the wider tires, I feel safer. Plus, I have a terrible problem with my sunglasses (or clear ones in rain/dark) fogging, despite all attempts at solving the problem.
What has changed for me is the temperatures I ride in. My lower threshold is pretty low now. In fact, it's gone from about 50 to about 32. While I don't plan long rides at cold temperatures, I feel good just getting out for 10-15 miles if the roads are OK. Snow, ice no way. That's x country ski season, which around here is very short and often involves travel to northern New England. I like the change of sports with the season.
The weather here is extremely changeable. So, I don't worry about not riding in the rain; once in awhile there have been years of more rain than others and it gets on my nerves. I started running a couple of years ago because of that. Generally, I will run or hike or walk in the rain if I feel the need to be outside.