1) How can I specify more than one file for StartFile? I tried coma-separated, which it didn't like.
2) Is there any directory listing support at all? If so, how do I enable it?
1) You can only specify 1 StartFile, but you can override it by using StartFile in a .hiawatha file in the directory that needs a different StartFile. It is faster to specify it via .hiawatha file then to make Hiawatha look for all the different possible startfiles.
2) Yup, just use 'ShowIndex = yes'. And with IndexStyle = /<stylesheet> you can alter to looks of the listing. See the manualpage for more information about that.
Please, keep me updated about your Hiawatha experiences. I'm always interested in some feedback in order to improve Hiawatha.