In fairness most of the time the site runs itself, but upgrades and maintenance can be a pain given that the site is using 3 different bits of software all developed by different groups. Probably something that comes up often is I have to keep increasing the space allocated to the server for all the images / attachments. We are at around 7gig worth of attachments and that's with relatively restrictive image sizes for attachments.
The video I posted was more of a joke, at Google I've heard engineers say that making major changes to a bit of software while maintaining uptime is a bit like changing the engine in a Boeing 787 mid flight. In this case it's not quite that bad because I'm doing a lot of the experimentation with the migration process offline, but the trick is to iron out all the kinks before uploading to the live environment. Making sure that when people log in for the first time the experience is relatively seamless (apart from the learning curve of the new software) and that everything is working as intended.
I've been working on it on and off the last couple of weeks as free time allows and as mentioned unfortunately very little has happened on the car, but on the positive side once we are on the new software I'll be able to whittle it down from 3 independent bits of software to 1 piece and all upgrades from that point on will be 1 piece of software. It also means making changes will involve 1 set of templates and I'll be able to more easily delegate roles to different parts of the website. So I'll be able to give some individuals access to publish content to to the homepage more easily etc..
In the long term it will also free up more time. It might seem silly but I'm actually looking forward to the time we move to Auszcar.com - which I've put off forever given the complexity of the move with 3 different bits of software.