Winter riding varies every year, but from the Springs you have the possibility of riding east just about any day (but, any day from Nov - Mar might also be a blizzard and 10 below). I live in the central mountains at 8,600' and I park the bike for 4 - 5 months every year. If the weather isn't bad, the roads are covered with sand, melting snow and mag chloride.
The cost of registration varies, with the largest part being a specific ownership tax that depends on the age and initial cost of the bike. It goes down every year and after about 5 years it is fairly reasonable -- a new C14, however, is going to be in the hundreds of dollars.
There is great riding out of the Springs: all the Colorado and New Mexico mountains, the grasslands, mesas, buttes and long quiet rides out to the east.