I have failed the OpenBSD challenge. Too many things just didn't work, and I had to restart into Xubuntu.
Getting most things working went swimmingly: I had a nice WindowMaker desktop setup, all my tweaks enabled, and I even wrote a little application for connecting to WiFi called
wim. Sadly, WiFi just had too many issues. I got to school, and while I could connect to the network, I had no connection to the internet except for a very limited amount of sites. I tried switching to
wpa_supplicant, but that spat out errors that weren't all that useful. I had such little to go off of to debug anything, that I just gave up. My current theory is because of my Intel wireless chipset.
Please don't take this as a sign to not use OpenBSD: if you aren't roaming, you don't use Intel wireless, or just don't use WiFi: everything else went swimmingly.