I do like the idea of supporting a DB-37, yes, jimstim and the rest support it, and it's still a very viable, low cost, readily available connector. The downside is the MS pinout is beyond salvation. it would be very difficult to make something both useful and compatible (but not impossible), so that the "extra" sensors and outputs used the extra ground pins. I'm still not against a power connector and a signal connector.
The multi connector board isn't a bad idea.
Really, my own personal vision is we get something out - something solid and simple - ASAP. Hardware is NOT irreplaceable, and by using stacking, we can replace one section or another in hardware without building a whole new box every time. I like the concept of hacking off what you don't need.
But for now, I'm still an advocate of a DB37 and a DB25 (or some similar combination of parts), and see 4 cars running on this. When it's working, and our horrible misconceptions and oversights become apparent, then we design something more akin to what you've got.
What I'm saying is the first release should be an alpha - in hardware as well as software. Let's stop worrying so much, get something working, then design it. And in the meantime, all this discussion is very useful, and means when the kinks are worked out, this sort of thing will be ready to go. (The nice part is it allows tweaking of the pin assignment without worrying about it's impact on the connector and other boards)