gus reiber, I'm going to leave it at Fridays for now. I'm aware of Daniel Beck's schedule; the website work doesn't generally involve him any more than any other plugin/core contributor.
...mostly what I am want to suggest is that it might be worth listing out where we might hope to be at the end of the year and then setting up some sort of demo day where we show where we are.
Why? I'm not being flippant but offering up process without an explanation makes it hard for me to understand why this might be valuable or important to you.
Anyways, the "deadline" that I'm really trying to work towards is wrapping things up with both the static-site conversion, and legacy->jenkins.io site switchover, by FOSDEM 2016.
As part of that, there's a ROADMAP.adoc which outlines some high-level efforts that have to come together before then.
Unfortunately this site isn't the only thing I'm responsible for, so I'm juggling it in with a number of other things right now