Re: Getting used to colder weather.
I give you my word of honor; I'm a cold weather wimp. Yet I can ride an motorized bicycle in single digits (Fahrenheit).
Once you learn how to dress, you've got it made, made, made! My only regret is that it took me so long to learn. I could've been a winter freak decades ago. But it took that long to figure everything out.
On a pedal bike I have to be concerned with overheating if the temp is above about 10 deg F. Though I'll admit that that's a different world than transport with a motor.
On a motor bike I do have to dress a bit heavier, it's true. But not enough to be a big problem. And I've ridden as low as 5 or 6 deg F and been plenty comfortable. Yes, the area around my eyes and cheekbones gets a bit uncomfortable. Maybe toes and fingertips, too. But if the cold spots are small, then it's not a big deal.