I think I know what's going on. The C API of most databases are limited to one statement per API call, and the installer tries to run several statements at once.
Since the installer doesn't know how to detect the end of SQL statements, it uses blank lines for detection. Thus this commit should fix it.
As for the HTTP side, you can use any of the servers listed on http://plackperl.org/#servers. I hear Starman is a good choice. Then an nginx or Apache as reverse proxy should be pretty easy to set up.
If you have any more questions, feel free to drop in on #ilbot on irc.freenode.org.