>probibly do Tuckerman Ravine Trail just up and down.
hmm... in winter this isn't really a trail, you're ascending a snowy/icy ravine headwall with likely avalanche risk. Good info here on SP: http://www.summitpost.org/tuckerman-ravine/155768
A generally safer route from the east is the Lion Head Winter Route. Still plenty of opportunity to get lost above treeline, but at least the avvy danger is basically nil.
The boots you mention look like a good general mountain boot, but they don't seem to have any insulation at all. Double plastics are overkill, but at least wear double socks.
Other than avvy, your biggest concern on the Rockpile is the wind. Watch the forecast and pick your climb day wisely. Easy to say you won't be "stopped a lot standing around", but a 100mph wind will keep you pinned down pretty effectively.