Use Word 2010's Numbering feature in tables and make it automatically number multiple table columns vertically. This way, each cell in each column will be placed under the correct number.

If you've ever been outfoxed by Word's page numbering options in a multiple-section document, here's good news: Controlling how the pages in each section are numbered is actually pretty easy ...

You can use built-in options to build a simple table of contents, but quite often, you'll need to change the underlying field code to get the results you want.