I have two VS projects, one for the main website and one for a \"static content\" website where all the css, js, images, and other static content will be stored and accessed
BundleTable.EnableOptimization = "false" isn't event coming in to play here, as your main site is referencing the "bundle", which is always going to be bundled and minified, regardless of debug status or EnableOptimization.
So @Styles.Render("~/bundles/styles") on the static site will render the individual files when BundleTable.EnableOptimization = "false", but if you navigate directly to /bundles/styles, you still get the minified bundle (what you are doing from your main site).
One option (perhaps your only) would be to configure the bundler on the static site to not minify the bundle when BundleTable.EnableOptimization = "false". This can be accomplished by writing a class that inherits from Bundle and uses it's own custom IBundleBuilder (you can even write the file name as a comment as you add each file into the bundle). Some example code to point you in the right direction can be found on GitHub.