Do your best to have one style sheet. Linking individual style sheets for individual pages defeats the purpose.
You can inherit other stylesheets in your css by including the following lines at the top of the sheet
@import url('blueprint/screen.css');
@import url('blueprint/styles.css');
in this case I'm inheriting the blueprint css styles then adding my custom styles below that.
In terms of JS libraries I prefer to link 3 files.
The Library,
one page with all of the plugins,
and finally the page code.
For directory structure I generally have the following:
/_css
/_images
/_scripts
files
but recently I've began to put everything used to make the site look/work the way I want it to in a /_presentation directory... then anything additional like images for blog posts etc would go in /images
Hope this helps.