I think it would be best to have revision boards in a kickstarter; sell the boards for one price and then full Pyra handhelds at another. He wouldn't be loosing any money on the full Pyra units but he could produce the upgrade boards cheaper in quantity. This way the existing community can upgrade cheaply, new Pyra owners will get full units quickly, and by that time the software will be more mature. It will also grow an already existing user base.
It is too early to be thinking about new SoC boards - assuming that newer/faster/updated SoC was what you were referring to. Much of the software that you're referring to maturing is directly related to specific hardware. I.e. a board revision would require two different versions of drivers and double the work in building and maintaining them. A new SoC would be more appropriate 1.5-2 years after the Pyra releases.
But - I could see where a Kickstarter might work for an alternate Pyra based product that would add publicity to the project and the current model.
*Pyramote
Handheld Pyra based bluetooth keyboard/game controller.
Uses Pyra keymat & nubs & shoulders.
Pyra main board with all of the underslung ports and slots unpopulated.
*Pyrathin
<20mm thick if possible
Pyra SoC board, keymat, screen, backlight. Relatively minor changes to main board to mount thinner peripheral connectors.
Half the battery, battery changeable with a screwdriver but not swapable (to save thickness of battery door clips).
Tall ports made thin. microUSB ports replace the USB 2 ports (at USB 2.0 connectivity) (Mainbord revision).
eSATA gone.
SD card slots changed to microSD card slots (Mainboard revision).
Case plastics made thinner - maybe even 'melted' to conform to contours of internal components.
No multi-layer screen lid insert. Just make the case plastic over the lid back LEDs so thin that they shine through.
Same underlying hardware and the same software as Pyra - just as thin as possible.
DOES NOT REPLACE THE PYRA. Just gives it a thinner sister device using the same technology.
I could see either or both of those working as Kickstarter programs. The Pyra itself is a provable prototype for either/both. They could be priced accordingly to account for the Kickstarter fees and discount. The Kickstarter audience would legitimately be funding the case plastics and board revisions to make them. They should popularlize the Pyra without stealing significant audience.