The current Python website continues to be a terrible first stop for new-to-Python visitors, despite this very issue being discussed at length at recent PyCons. Compared to the excellent Git and Ruby sites, for instance, it's really second rate from a design, navigation and identity perspective.
However I haven't pursued contributing to the site. Here's why:
1. Contribute to the website options on Python.org seem limited to "bug fixes". The "SiteImprovements" page is a mess. The whole site design and identity is a bug, unfortunately.
2. The stagnant design (only a marginal improvement over the previous iteration) implies that there is either a serious design-by-committee problem when it comes to the site or a serious lack of good-design-sense from whomever is actually running it.
I'm not trying to be a grouch about this, but the site needs strong direction in terms of visual identity, navigation, presentation, etc., not just incremental fixes.
I'll put my time/money where my mouth is on this. If there really is a chance to radically improve the site and contribute, I'm there. Point me in the right direction. If there is a roadblocker committee issue that needs to be sorted first.
My all time personal favorite project website is openbsd.org.
After one experience like this most people would be ready to submit patches on their own...
I think it would be cool to have the community provide this sort of "training wheels" to help people get past all of the roadblocks and not feel relegated to dealing with bug report paperwork (as valuable as that is)...
The conundrum with projects like Python is that the people talented enough to submit useful patches are usually not the ones who have the time to do so.
As for me, I find it is a lot easier to contribute to smaller, less developed projects. There is more to do, and I feel I can have a bigger impact. Also, its less intimidating than big projects, you don't need as much domain specific expertise with smaller projects.
Though I have looked at Rubinius (Wishing they had a better name :/)
Most of the standard library is written in Ruby, and my guess is that there are things in there that could use some love.