I can only comment on the boots. I owned 3 pairs of Ride Jackson Boas. I really liked them, but A) they are a fairly soft boot, and B) they pack out and get kind of loose. After a season or so, I tended to have a problem with heel lift. So get the smallest size you can get into. The end of last season I bought some 32 Focus double-boa boots, which I like much better. They're a harder boot, and the double-boa gives you the ability to crank down the top of the foot better. If you're dead set on the Jacksons, get some really good insoles to even out the footbed a bit.
I hate the parts between winter