@Dalerhoda perhaps you would like to write something up as part of the "Dirty Jobs" funding proposal that will be going out on Sunday? Ideas wanted: Up to $25,000 USD available to improve ODK - #11 by LN
Incidentally, @jwishnie is one of the people behind that funding opportunity. Does this kind of usability testing seem to fit what you had in mind, @jwishnie? Perhaps this component of the proposal could include evaluating the current state of date widgets, writing up better training documentation and mocking up other possible future changes.