So... I installed ssh and I'm ssh'd into my work machine. I then loaded gedit and the source for a project I'm working on. I can do everything (scroll, menus, highlight, etc) 'cept type from the OSK. Maemo doesn't seem to recognize the gedit window as an input field, so it won't pop up the OSK.

Is there a way to force the keyboard up?

Not easily.

There's been talk in the past of writing a small Gtk app which solely exists to open the VKB and pass events through to the window below, but AFAIK it's never been written.

Using a Bluetooth keyboard will work, however, as keystrokes here go straight to the X layer rather than Gtk+ on the device.

That's a good question. The 770 and N800 both need a way to force the onscreen keyboard to show up in order to interact with some websites, especially those hosting flash games. Many games expect keyboard input.