I'll take a stab at it...but you likely won't get the type of answer you're hoping for. The home you're looking at buying isn't a Butt-and-Pass style log home, the building design we deal with most on this website.
If it is the cabin I think you meant to link to (that link took us to the general listings page) on Wee Burn Drive, then the exhisting dormer is stick-built to begin with and making a dormer to match it on the other side wouldn't be nearly as difficult as trying to put in a log wall dormer. That said, I've lived in Juneau before and their building codes are a pain. If you're planning to do this yourself, the biggest issue is trying to build the dormer while not having to replace the whole roof, and obviously keeping the structural integrity of the roof and second story floor, etc. If you're planning to have it done by a contractor, then I'd try to get a price quote or talk to a few to see what they say. Of course, that'll cost you a good penny too!
One, perhaps simpler option if planned well, would be to enclose some of that open ceiling space I thought I saw in the pictures. If you could perhaps beef up the rafters there if needed (or add extra) and then extend the 2nd floor over that area, you'd easily get another room or loft area for future expansion. That may not be as asthetically pleasing, but then you wouldn't have to mess with the roof and I'd think it would cost much less and be less of a building code nightmare as well.
Please do some thorough research on log homes and what maintenance and upkeep will be required of your specific cabin before taking the ownership leap.
Best of luck! Juneau is a crazy realestate environment.


My wife and I are looking into buying a log home that is 2 bed-rooms and 1200sf. We need to add another bedroom to the house to make it work for our growing family. Here is a link of pics of the house we are looking into buying.
http://www.isellalaska.com/Nav.aspx/Page=/ListNow/Default.aspx
We would like to put the dormer off the back of the house where the existing dormer is. Any ball park estimates on cost/difficulty or any ideas of how to add another bedroom onto the house?
Thanks for any help