"One thing I noticed is that they're having a hell of a time transitioning away from the traditional sysvinit-based system to the Upstart event-based init daemon system."
That's syntactical stuff, who knows. That rabbit hole is as deep as your project made it. Strategically, OBSD does less, but does it very well. Linux will claim 5 times more features than OBSD, but only a third of them work as advertised and that third is a moving target from one release to the next, without saying one is better than the other, it just depends on your needs. I think the bigger question is why are you moving from OBSD to Ubuntu?