I think the initial source of confusion was how the man page was formatted.   It was something like:

<b>roundup-server</b>  [options] [<b>name=</b>tracker home]*

I assumed that meant you could do something like "roundup-server name=/home1 name=/home2".  IOW, it was not clear that "name" was variable, not literal.  That seemed logical to me since with just the home directory the config file could be parsed and the URL for the tracker found.

Aside for the formatting (maybe that's just my man implementation or my terminal), I guess the documentation is okay.  What about the "web" setting in the config file?  Does that need to match the path used for "name"?

Perhaps the easiest "fix" would be to print a warning in the log when the "name" or "web" setting does not match the request headers.  In my case I had no idea I had configured something wrong, just that I couldn't login.  Another idea would be to do away with the name variable passed to roundup-server and use the "web" URL from the config to figure things out.