I want to combine the page and category menu.

I'd like to have a consistent navigation menu in the left side bar on every page that consists of both the static pages and the categories listed together under the title of "Content".

A smaller question right off the bat, though, is that the Pages List is not showing up in either side bar even though it is checked. I haven't changed the default settings for the side bars so all the widgets are checked for both side bars. (Which is kinda confusing. Seems like they would all show up on both the left and the right sides but they don't; they are split between two sides.)

Anyway, back to my original two questions:
1) How do I make the Pages List show up in the left sidebar? I have two static pages now but will had more.
2) A longer question: how do I combine the page and category navigation menu.

Many thanks!!!