Here in one of the two rain capitals of the USA, it rains about 8 months a year. It does occasionally get into the high 20s, but not often, and when it does it is almost always dry. I find those days a cakewalk. We have had zero snow so far this winter. Could snow this weekend, though.
All that said, we have many, many days of lowish 40s/high 30s and lots of rain. Very common. It is just unbelieveably cold when it is like this, esp. if it is windy. The key for me is to try to stay as dry as possible wiht the appropriate gear, as mentioned above. I find feet particularly important--I wear some Showers Pass waterproof socks that do help a bit. Sadly, though, if I am out for more than 2 hours or so, it is just super hard to ultimately win the warmth war. Even if you think you are warm enough, you may discover when you return home that you were, in fact, not. I have had the experience of not coming in soon enough and then shivering--inside--for a couple of hours. More than once. I misjudged how cold I really was.
So, this type of rain plus high 30s/low 40s can be quite dangerous, in my experience. I really don't generally recommend people to be out in it for more than maybe 2ish hours or so, unless they have killer rain gear and some prior experience successfully doing it in that gear.
Weather is weather. You get used to what you have where you live, usually.People in Phoenix hike Camelback in July all the time. People on Oahu know when it is dangerous to be out on the water. They know how to do it and not die. Like most things in life, it seems like local people are the go-to folks on what is safe and what is not wherever you happen to be.