We've heard this a lot, and I think many of us on the team do still have a soft spot for the current site. It has served us well over time, but it's really time to grow the site along with Python - the language, the community, and everything that goes with it.
One of the biggest parts of this redesign is happening on the back end. One thing I look after on the site is the PSF board resolutions and minutes pages. Oh you see a typo in the latest page? Here's how you fix it:
Get to machine that has the checkout > svn up > edit file > rebuild website locally > run webserver and check local instance > svn ci > wait for server cron job to catch the change and update the live site > confirm on live site
That sucks. For me it's not unworkable because it's not far from what I do as a developer, but it's definitely a hassle more times than not. However, getting less technically savvy contributors is not very easy. We had an administrator who was tasked with updating the pages I look after, and this person didn't know what an SSH key was (not their fault). The whole thing became a non-starter.The new backend will continue to support the developer-like workflow (which really is good in some cases), and it'll support online editing which will be nice for a lot of things as well.