Thanks Samiux, that article is pretty useful
Thanks Hugo.
Basically HTTP error and drop connection are rules that you can set on a file/directory within Cherokee so that it'll automatically serve a 404/405/500 etc error OR just instantly drops the connection if someone tries to access it. The static content rule basically bypasses any more advanced server functionality and serves up a requested file/folder.
I'll check out creating aliases. Thanks again. I think Hiawatha might just become my new default server