Jeff your project and your assessment that “web” is your webroot are actually all exactly right. The reason your paths like your IMG example above don’t work is because of how you are deploying your app and how the browser resolves the path, this isn’t a problem with you or your project setup.
Let’s say your domain is http://www.jeff.com, from your example above of “/web/img/clear_dot.gif” for your image, that means you have to have an image at http://www.jeff.com/web/img/clear_dot.gif
however, when you setup your project as a web project, chances are when you were asked for a web context root you had something like /myapp in there. So this actually gets deployed to the “myapp” dir under your Tomcat webapps directory.
So your GIF will be here: http://www.jeff.com:8080/myapp/web/img/clear_dot.gif
If you change your web context root to just /, MyEclipse will deploy it as the root app, so it will be here:
http://www.jeff.com:8080/web/img/clear_dot.gif
and if you want to run your server on port 80, then your path will look like this:
http://www.jeff.com/web/img/clear_dot.gif
hope that helps clarify things.