Thanks very much for your detailed response! And the CSS snippet you whipped up. Very helpful.
A couple follow-up questions: I appreciate the CSS snippet you made and it is indeed fairly close to the design. However I know it's not possible to style the actual dropdown itself so would that require editing the plugin layout file itself, replacing the <select> structure with a
structure instead so that it can be styled?
Regarding the datepicker, that makes a lot more sense. Would this be possible by utilizing a custom field rather than creating a whole new taxonomy?