Bill Janssen has suggested reviving the Web SIG: http://mail.python.org/pipermail/meta-sig/2003-September/001277.html
SSL server support
Add SSL server-side support to the "socket" module. This will include some way of managing certificates. Probably modelled strongly after the way we did it in ILU, if [Bill Janssen does] it :-).
HTTP client updates
Update the "httplib" module to include all of the client-side functionality available in the Linux "curl" program (a reasonable checklist, I think, but am open to better suggestions).
Better support for HTTP Digest Authentication.
HTTP server improvements
Replace/extend the BaseHTTPServer and SimpleHTTPServer modules with an extended webserver module which provides at least the functionality in Medusa.
cgi module improvements
The cgi module is really old and has a number of obsolete classes. It should be cleaned up and modernized.
Anecdote: file upload support in Quixote was unreliable until Greg Ward threw up his hands, ditched cgi.py, and reimplemented file uploads from scratch.
Add request/response objects to standard library
This has been brought up on the pyweb mailing list.
Add a module containing the HTTP status codes.