My volunteer position is saddled with some unfortunate server circumstances, most notably a chat CGI that is -- forgive me for ripping on someone else's code when I've never produced a reliable project myself -- almost completely uncommented and designed in a rather incomprehensible fashion.
Currently, most of the to-do list consists of feature requests for this selfsame chat program. (In fact, one of my great suggestions was an attempt to produce documentation for the chat CGI.) Like so many other places, it was "the best solution at the time and now it's just there".
It recently occurred to me that a true solution lies in conversion to an IRC server with a CGI gateway. (It's not an option to discontinue CGI access altogether, due to needs that apparently need to be met for WebTV customers.) Were a rudimentary IRC server functioning and a CGI gateway providing CGI access, most problems would essentially be solved -- all the feature requests like IP bans and whatnot are already implemented, and the little pretties that have to stay in for other reasons could be kept in the CGI client.
Of course, I'm just talking out my ass here. I have to actually convince someone else of this, and they may not want this solution, it's a lot of work for perhaps not enough result, etc.