Thanks for your patience here - I can see we owe a more detailed response! To be honest we don't have this planned in the short-term roadmap, as we do have work-arounds like using categories or tasks from workflows. For more advanced triggers in the workflows (based on date/time), we recommend Globiflow available on Premium.
I still think this is a cool idea but no news on implementation of this in the near future.
One question - what is the main difference in functionality between categories and the checklist (other than the design of the box)?
//Sara - Podio