I wear contacts whenever I'm doing some kind of outdoor activity -- hiking, backpacking, cycling, etc. It never gets real cold here in the San Francisco Bay Area so I don't know how the cold affects wearing contacts. I do get dry eyes from time to time, usually when I'm tired or didn't sleep enough. From time to time I carry on me a small bottle of "rewetting drops," which is in effect some very expensive eyedrops for your contacts. Usually after riding a couple of miles, my eyes adjust to the outside environment and I'm OK.
Re. toric lenses -- I have severe astigmatism and have to wear toric lenses. The thing about toric lenses is that they have to be rotated in a certain way in order for them to work. So they're weighted toward the bottom and should settle naturally in position when your eyes are properly hydrated. When you first put them on and your eyes are dry, it'll take them a few mintues to settle in.
I've found that not all toric lenses are made the same. I used to have these expensive Baush & Lombe lenses and they sucked. I could never see anything clearly or read anything upclose, and wearing those contacts always made me dizzy. Then I went to my local Costco where they have an in-house optometrist and the doctor said, "Those contacts you had don't work too well and you were probably getting only 60% of your vision with them. Here, try these..." He prescribed some "AcuVue" lenses for me and they felt like new eyes! The doctor added, "Unlike before, you should be able to wear these contacts all the time without feeling any problems." For the first time, I was able to see clearly and read text without squinting while wearing contacts. They were comfortable and I didn't have headaches anymore! So my point is, shop around and make sure your optometrist knows what he's talking about.
BTW, I also wear disposable contacts. I've found them to be much better than the permanent ones because with the disposables, you only wear them for a couple of weeks and throw them away and put on a new pair. That's much better than wearing the same pair for a year because old contacts do get scratched up and they may damage your cornea.
Good luck!
-Kevin