I looked at your booties, and thought, "for just $20 more you could buy a pair of Western Mountaineering Expedition Booties" but then I thought, well yeah... for $20, $40, or $100 you can get all kinds of stuff. :)
But, when I noticed you are also thinking of purchasing new boots that appeared to be over a hundred, I wonder if you would like to look at Steger mukluks?
While they are most effective in arctic conditions, as you are looking into to doing overnighters, and continued day hikes, after adding some water repellancy to your boots, they'll likely keep you happy. A hiking boot, and camp shoe all in one.
The Steger mukluk website is very helpful in getting you the best boots for your environment. Again, better conditions for the boots are -20 and below, but they sell boots that with care, will comfort and protect you in -10 to -20.
LINK to a BPL users thread: http://www.backpackinglight.com/cgi-bin/backpackinglight/forums/thread_display.html?forum_thread_id=6293