I was born here, spent winters outdoors and honestly it’s not the worst. It CAN be pretty miserable at times tho, especially if your unprepared when storms come thru. You should be able to stay comfortable enough with pretty average winter gear, definitely have some waterproof layers. Expect a lot of rain, often times it’s light or only a drizzle and not bad to be out in. Other times you will need to shelter. Sleeping outside it rarely gets below 30 degrees, usually temps are something like 30-40 at night and 40-50 in the day November-March. It’s a humid,wet cold tho, and it really soaks in. Winter can be pretty comfortable if you have your situation figured out. One thing I will say against all this, is that actually staying on the move can be sucky and takes some planning. The weather changes constantly and unpredictably, and your going to end up stuck in the rain at some point or another.