Here is a proto-prototype for the pcb version (I needed another guino for testing anyway). It was a PITA, took some planning, but it is loosely based on the pcb planform above and uses the same schematic. Playing with the layout in eagle helped out a bit.
For some reason this lcd isn't turning off all the way, no biggie. But need to figure out why.
The onesided preprogrammed version currently only has one airwire, and needs some tweaking yet. But I just checked futurelec and their price per board just took a big jump?!? 10 single sided boards would be $39 shipped. And that is with doing your own custom buttons. Where are we with the buttons anyway? I've gotten pretty good at fabbing them and tucking them into the LCD border, but that doesn't make it the best solution.
Also don't know about programming headers or onboard usb/rs232 chips. I'm comfortable using my existing freeduino to program a "headless" guino chip and pop it in to the socket, especially if the software gets pretty stable. I could crank out quite a few of them for friends and family who would never have need for either the usb chip or a programming header. Is assuming the builder has an arduino at their disposal to program the chip setting the bar to high?