Hahaha oh yes. The pit. We moved offices, so we don't have a Pit anymore... It's really sad, but there's an alley that's probably even more dangerous.
Humo(u)r is something we have a knack for just because of the team chemistry. We make jokes in games just as a part of being in the office together. It's a weird, cool experience, and a great way to manage the stress of game development. It actually got a little out-of-hand with Dungeons of Dredmor. At the time, we just put in what we thought was entertaining because it was the sort of game which should: it really matched the tone of the art and alleviated a lot of the stress of playing roguelikes.
With Clockwork Empires we're putting a bit more of a filter on what goes in. David, Nicholas and I each do a bit of policing on the content to make sure that the tone stays just right. CE is not zany like Dredmor. The humor is very dark, partially because it fits the setting, it informs (and is informed by) the art, and giving players decisions that they should feel a combination of guilt and satisfaction from are very interesting and worth talking about.
So we make dark jokes all the time, there are some in Dredmor, we're just filtering out the random pop culture stuff and focusing on the things that are period appropriate, a little macabre, and some that are just sort of British for the colonial angle. The frontier has always been an exceptionally dangerous, dirty, horrible place, filled with pain. We want to show that a little bit, but give it a stiff upper lip and make that entertaining and enjoyable.
As far as capturing the process, it's an interesting idea. I have thought at one time or another to just put up a webcam, but if you've ever watched Notch stream dev work you'd know that it's 99% very uninteresting entertainment. We grumble and we type and we drink lots of coffee. There's also a fair amount of stuff that isn't PG, and what is interesting and fun to watch wouldn't happen in a specific context. It would just be too difficult. The best we can do is to provide video interviews now and then, as our enthusiasm and camaraderie pretty accurately seems to come across in those. I keep joking that we should publish a book based on our internal blogs, wiki, commit messages, and tweets, but now there is no time, there is only the deadline.