I had fixed the issue. Instead of using nullfs to get access to the /usr/home directories, I am using unionfs, which basically does the same for my goals (unless someone corrects me in misunderstanding things) and this does not seem to generate the same issues. Various sites are now running happily behind the WWW Jail. Time to finish my document on how I did setup the entire beast.
Thanks all for listening, helping, and giving tips (Alexander and Miroslav!)