Travel to Japan in December

Planning to travel to Japan in December and the cheapest nonstop flight I can find is slightly over $2000 CAD. For those that fly to Asia from North America, do you find that this is a good price? I am not a frequent traveller so I am not too sure about a lot of stuff.

Another question I have is how layovers work. I've noticed many current flights that are cheaper ($1600 CAD) have layovers. Do we have to pick up the luggage during the lay over or do the airlines transfer our luggages for us?

Thank you!