Rails is the best thing that ever happened to Python
antoniocangiano.com
antoniocangiano.com
2006: http://www.garbett.org/files/books.jpg
2008: http://antoniocangiano.com/images/rubyandrailsbooks.jpg
Its a detailed comparison between the 2 frameworks.
Unless there's something specific you dislike or have a strategic reason to switch you should stick to what you know best (either Ruby=>Python or Python=>Ruby).
I think Pylons has broader and deeper goals, so there has been a period of ramping up and getting the foundations in place, while the efforts put into Django's development have been focused on making specific things easy. Now Pylons is settling down and maturing, it will probably start to become much more widely used and appreciated. Also, Pylons may benefit from Django's recent boost in a similar way the link suggests Django is benefiting from Rails.
Sometimes I think the included apps in Django too heavyweight. I get a lot of "just because it's included doesn't mean you have to use it" and "don't re-invent the wheel"/NIH responses from the mailing list.
Answers to that may change the game somewhat (both can be made to work, but which one lets you work better?)
If you need a quick database driven website (less of a webapp) then Django is perfect, I find the included admin is a real timesaver.
And here is what I think went wrong:
1. White Space, syntax does matter and so many people where turned off just by the syntax choice of white space, its just annoying
2. Zope, this framework always had a popularity of being too complex, Zope 3 was a rewrite to fix the problem with Zope 2, Guido worked for Zope for a while, I thnk he left, if start looking at Zope and see it was rewritten from scratch, you become warry, Zope till today have the reputation by being too complex and forcing you to learn new zope specific languages
3. Twisted Matrix, it also had a reputation of being too complex and it didnt serve a common need anyway, what the heck is event driven networking anyway! And their community, sooooooo exclusive
4. The community, a lot more interesting ppl use Perl and Ruby, do you know of any cool blog by a pythoneer? do you know any cool pythoneer? even Matz is cooler than Guido, and Matz isnt even cool! Open source project need people considered to be cool in their community, Dan Short was the only cool Python I remember, he disapeared I dont know what happened to him
Zed Shaw also occasionaly drop a good word for Python but trust me, if he digs deeper into Python, he will backlash.