No, I'm still stuck. Not sure where to go from here, so I'm starting over with a fresh install of the OS. Perhaps I'll pick something with python 2.6 ? Obviously I don't have to implement the ssl through python, I can make the connection through another web server, but I hate to give up after investing this much time.
I'm still going to try and use the included CherryPy server for my testing because I'm stubborn. I just can't get the python 2.5 with ssl to work under Debian without compiling it myself. I wanted to keep stability on the server and use the package manager to add programs. Perhaps something like CentOS would be a better choice. Once again, thanks for your help with the problem.