I'm switching to SMD components now that I can comfortably work with it. And because of that, I can make more of the real estate. I'm going to integrate the LCD backpack circuitry on the board and mount the LCD on the back, along with all of the terminals for connecting up to the outside world. The board will get mounted upside down and the whole thing should wind up being mechanically easier to deal with.
The board design is up at OSH Park. I haven't quite pulled the trigger yet to order a prototype. I want to ponder the design and layout a bit more first.