I started with this whole web framework thing writing my own crappy code in perl. I found python, loved it, and immediately started learning django (the 0.96 version.) I quickly became dissatisfied with the limitations of the framework as my apps grew in complexity. This was somewhat in part due to new additions like newforms that were not yet completed or fully integrated. Currently I'm using the pylons framework and I am absolutely loving it. It sounds like if you are even 'considering' writing all the code yourself, you should really pick a framework akin to pylons or web.py in your language of choice. Ruby, Perl, Python, it's really all the same...