This is my setup for bootstrapping a static web project with using Compass, SASS, and HTML5 Boilerplate.
All Compass and SASS related files are in the /compass folder.
The config file is set up to be ready to go. For your edits in /compass/sass/ css to be compiled automatically, run the watcher command compass watch within the /compass folder. Then all your changes in the SASS (.scss) files will be compiled into the /css folder.
The base CSS file (/css/style.css) is pre-compiled using the HTML5 Boilerplate approved normalize.css. If compass is watching the /compass/sass folder then all your edits will truncate over styles.css. Make sure to only edit the .scss files.
Libraries are stored in the /js/libs folder, including jQuery and Modernizr. There is a starter file (script.js) supplied so you can start writing base JavaScript, but feel free to replace or use other frameworks and libraries to your choosing.
Create a folder named /img at trunk level and place your images there. You can also create additional folders to use with the Compass spriting engine (make sure to include @import "sprites/*.png" in base stylesheet).