Nobody would re-implement TLS in a garbage collected language, at least if they planned to use it. There are libraries for that. And who kn their right mind would implement PDF parsing themselves? The more I familiarise myself with the PDF format the happier I am with the libraries that exist.
I did write a web app that served a couple of hundred people with information, chats and live updates at a conference a friend was hosting. It was written in guile and made heavy use of delimited continuations which is probably my favourite way of handling state on the web. The main logic was less than 2000 lines, so it was by no means a large project.
What about the unicode handling would be shaky? And why do you say handling unicode is simple?? :)