Hi ya Bare Feet,
When you got to the part of your post about huffing and puffing when you first began I thought, "Hey, that's me" From h'ing and p'ing last spring when I first started cycling, I now ride 30 to 50 miles, 70 to 100 per week. After buying and trying a number of saddles, I finally have a keeper and can venture into territory beyond 50 miles. For next summer the goal is a century. Like you, I just got clipless pedals but have not tried them yet.
Here in Rhode Island the Narragansett Bay Wheelmen have rides scheduled throughout winter; I'm assuming barring snow and ice on roads. Last spring I rode in quite cold weather. I already had very warm clothes from hiking and skiing. With good woolies underneath, gloves, face mask, windbreaker, in 5 minutes of riding you will be nice and toasty and wondering why everyone else is so bundled up. Find your local cycling club riding partners and tips.