I think we've made a lot of improvements in our process recently: the autofill submission forms; autofill certificates; folks submitting on line; being able to send completed maps and certificates to Gene and Justin online.
Adding the "essay question" to the application form was a good step. It sounds like it is underused, so I'm thinking we should really push for measurers to at least write something there -- could be a narrative, or special problems they faced or solved, even saying what was fun or miserable about this measuring project.
In short, I would favor continuing with incremental steps like the ones I've listed-- some of those steps might even get us closer to the sort of thing Lyman is talking about, while some could be in other directions.