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.