By the way, is this home platform framed or balloon framed?
If the living room and bedroom walls are exactly atop of one another, try locating your outlets in the same wall cavity, so you can pass the cables from the bedroom partition wall to living room partition wall... then all you need to worry about is from where is easier to branch off to the source(s) (bedroom wall or living room wall).
If the house is balloon framed, the living room and bedroom "partition" wall could be load bearing straight to the roof, so there would be no drilling upstairs to downstairs. Also above the second floor, the cable could almost roll down the slanted ceiling into the side attic "crawl space".
I think the most helpful thing you can do is get some diagrams on home framing... this will give you the "X-ray vision" template on what your possibilities might be for running the cables.
Good luck!
Joe
