Well it sounds like you are at least thinking about it.

Some very general reccomendations, rather than addressing each of your points.

1) a number of us post gear lists - there are some on this site that are nice. mine is
linked through my profile, click my name, start there. There are some good reccomendations.

2) You talk about 4 seasons with some winter. I find carrying winter stuff around all summer to be a big heavy pain in the butt. - that's why I essentially have a seperate kit for winter, and my
winter is pretty hardcore.

I don't use mountaineering boots even in winter. Snowpacks or insulated hiking boots with gaiters
and snowshoes. If I did winter mountaineering I might use them.