Another option to getting a bear out of the woods whole is to buy a Deer Sleigher. They come in two sizes - the smaller one works good for a whitetail, but the larger one should work good for a bear - assuming it's not a big griz or brown bear.
The Sleigher is just a piece of heavy plastic that rolls up and can be carried in a back pack or pack frame (vertically). It has grommets on the sides and parachute cord included so that after you lay your bear on it, you lace it from side to side to hold the critter in.
There's also a bigger hole in the front to put the pulling rope through and around the neck of the bear.
It pulls just like a toboggan. Really slides nicely on pine needles or dry leaves, and REALLY good on snow. I have pulled whole whitetail out several times, and it's a real work saver.
It sounds to me like the best idea, given your inexperience with skinning, etc. would be to locate a taxidermist in the area you'll be hunting, then take it to him whole. That way you wouldn't have to mess with freezing, shipping, etc and then back again.
It would be one-way shipping to you after the rug is done.
I'm guessing that if you made arrangements, he'd probably either help you or show you how to get at least some of the meat to take home.