I lived in Southern Anchorage, in the Dimond area. I'd probably stay away from Eastern Anchorage, around the Muldoon area.
Hillside is nice, but $$$ and can be a hassle in the Winter. Just remember, the further outside the center of town you are, the longer it takes the snow plows to get to your street.
I wouldn't worry about bears as much as I would moose. Those are some mean critters! I've got more than one moose story I can tell from living up there.
There are a few tris in AK, including a 1/2 IM. Go to
www.trifind.com