Thanks for taking the lead on this. I agree with everything you said, except I don't think the state certifiers, vice chairs, or registrar necessarily need to be any more electronically savvy than they currently are.
I would suggest the following small change to your procedure. The state certifier can do everything the way he does now, except that in the end he doesn't mail the map or certificate to the vice chair. Instead, once he is happy with the map and application, he asks the measurer to create electronic versions of the map and certificate. When he receives those from the measurer he forwards them on to vice chair, just like he does now with the paper versions.
This system doesn't require anyone to learn anything new, with the possible exception that the certifiers would need to be able to confirm that the electronic files they receive are in the correct format before forwarding them.
And of course, any measurer who wants to submit everything in paper can still do so.