Maybe you could buy a special trunk for any house. When you open it up you can put in or take out items and it gives an option to have it transported to another house you own (a drop down menu or something). It would cost money dependent on how far away the trunk has to go. It would be "picked up" and "delivered" by the towns delivery service/coach system. But that seems unlikely to be an option in any form in Skyrim. You'll just have to lug it there yourself.
I liked the luggage from COBL, it was basically a container that "followed" you by being in inns, camps, etc. I am pretty sure it was just multiple containers that shared the same inventory. Not very realistic, but I liked it.