TLDR: Our scheduled maintenance has gone according to plan and with a lot less downtime than originally expected.
For those of you who are interested in exactly what we were doing, here is a breakdown.
Up until now, I'd been hosting the website server and Joe, the blog. This setup had been working for us, but managing operations between timezones can become difficult. Our singular DigitalOcean account houses both our blog and website servers.
Cachet Status and Demo are no longer on Heroku
Since the early Cachet days we were running our own status page and the demo on a Heroku instance. However, with their pricing plan changes and our upgrade to Laravel 5, Heroku were no longer an ideal fit for our needs.
Our demo will now reset every 30 minutes now.
Website deployment with Envoyer.io
As huge fans of Laravel and everything it does, we're not only using Forge, but Envoyer.io too. This handles all of our website deployments with zero downtime.
In the future we'll probably move our status page and the demo to Envoyer too so that we can deploy everything with little fuss.
All in all it was a huge success and I for one am now relieved that we're running the latest version of our own software!