Here are mine:
My first winter car was an 89 Lincoln Town Car... bought it from a guy locally for $600, I drove it for 2 winters then sold it for $360 so it wasn't a bad deal at all! It had over 200K miles on it and had it's little issues, but ran and drove great. Eventually the transmaission started to go and that's when I sold it. Wasn't the greatest in the snow being RWD but I made it around ok, a couple 100lb bags of sandblasting sand in the trunk helped quite a bit. Not a very cool car but damn it was comfortable!
After the Lincoln, I bought a 91 Chevy 4x4 1/2 ton pickup which I had for about 5.5 years. I had some issues with it initially (which I talked about on this site) but after I got the original problem straightened out it treated me well. I sold this truck this past summer.
My current truck is a 1983 Chevy 1 ton 4x4. It was owned by my grandfather and has been a garage queen for a long time (it hasn't seen a snowflake in 20 years) The truck has about 60K miles on it, 350, TH400. I also have a snow plow for it (although I don't know if I will be able to bring myself to plow with it, it's in such nice shape.) I made some slight changes to the truck, one being new tires 285/75/R16's with some nicer looking wheels. Plus I spent about a month fixing up little odds and ends to bring it back to looking really nice (the trim was falling off, did some serious detailing, etc) Also did lots of routine maintenance type work to it since it had been sitting quite a bit. The old wheels and tires will go back on for winter. Now that I have a 1 ton truck , I was finally able to get a pickup camper. I've wanted one for years to take out on the beach but never had a truck big enough to put one on.
The first pic was right after I got it all cleaned up and on the road, the 2nd pic is with the camper on it and the new wheels and tires
So there they are... I only drove the Olds for 1 winter so far, that was before I bought the Lincoln. Now the Olds only comes out when the weather is nice!