Natalie,
I am posting this link to winter sowing because it answers some of the questions I had about it.
My big worry here would not involve the cold weather so much, but the warm weather. There is a lot of similarities in "winter sowing" and using a cold frame. By far the biggest danger when I use my cold frame (there is some danger from freezing weather) is the heat build up. If I am not around to open up my cold frames my plants will fry even in the winter when we have a lot of days that get up to 70 degrees sporadically.
I am a little concerned about Natalie saying " I was going to put them in a large covered plastic container". There would have to be lots of drainage holes in the bottom of the container(to keep plants from drowning) and lots of vent holes in the top (to keep the plants form frying and to let in moisture when it rained), or you would have to be physically present to open up the container on warm days, close it on cold days and that defeats the purpose of winter sowing. I think of winter sowing as being pretty much "set it and forget it", but still even using the typical milk jugs, it seems on warm days extra venting would need to be done (I know it does here as the weather begins to heat up and the plants start to put on leaves.
I am not saying that winter sowing cannot be done in paper containers, but it just seems milk jugs and soda bottles are a better fit design wise for "winter sowing". When the milk jugs and soda bottles are placed outside, the lid is left off, for air and moisture.
To answer the question about transplanting the seedlings, if the container is sown with hundreds of seeds they would have to be dug out in groups, but if only say...1 to a dozen seeds are planted and the seedlings transplanted when they are small it is easy to dig the out one at a time. The point being that for some plants one method is better than the other, but they both work.
http://www.bachmans.com/files/...