I think I'm on track for a 1000 mile a year running distance, I just haven't kept count. Started running every couple days 10km to get some groceries last July. Now I'm running 10km going to train jiujitsu 5 times a week. I've always ran a lot just not regularly like this.
So far its been pretty much easier running in the winter and its been getting colder than -15c. The only problem with winter running is the cold air so all you have to do is put some sort of face mask over your mouth and it'll help warm the air you breathe. It's also not a good idea to start doing more exercise than you are used to in the winter just because it is so easy to get sick; if you eat enough you should be fine.
If I might make a suggestion don't try to make your stride too long. Shorter strides with higher turnover is actually more efficient. By landing more towards your fore-foot it allows you to use the elasticity of your Achilles tendons to return up to 30% of your energy into the next stride. As an added bonus you should feel less pain in your feet, shins and knees.
Elite distance runners average around 180 strides per minute and short strides where your foot doesn't land too far ahead of your center of balance are key to achieving that turnover.