I have been using Workflowy Pro for about 1 year, every day, many times.
The problem of missing dates is solved using keyboard shortcut in PhraseExpress (Thanks, Frank :) this way #d_2016_05_19_Mo
I have a two main outlines: Inbox and Projects.
Here are some ideas about current date behaviour and the vision for future
No date reminders, only saved seaches with dynamical date tags. Please, keep Workflowy simple! :)