Kevin, to be helpful we'll need to know where and how you're going in the Sierras this winter. Given the overall tenure of your post, and the fact that you're planning on snowshoeing, I assume you don't yet know the answers to these questions yourself and will spend the winter finding out. That said:
-Stay away from avalanche terrain. Learn enough to know how to do this. It will mean lower elevation terrain, which will make it possible to use your hammock.
-That said, I'm not a hanger myself, but I can't think of a shelter which would work well with both a wood stove and a hammock. You'll loose a lot of the heat with an open tarp, rather than the pyramid shelters traditionally used. If you plan to expand your winter skills for years to come, I'd get away from hanging. Not so good above treeline.
-Opinions vary here, but I don't think hard shells are a good idea in winter. Sometimes they're necessary, but if you can get away with a more breathable windshell you'll be happier in every way.
-No need to wear mountain boots unless you're climbing ice or steep snow. They suck to hike in, and there are more appropriate options which are just as warm and cost less than half as much.
-If you have any questions attached to an ice axe, don't buy one or get near anywhere you might need it.
-The Frostline has a rather low fill/overall weight ratio. There are more efficient warm jackets.