I appreciate e time you spent on this post. Lots to think about here.
I am curious - how do you actually set this up in Toodledo? For example, do you have a Routines folder? Do you set up a folder for each goal? Or, are you using tasks/ sub tasks?
When I try to add a new task on my laptop (which is running on Explorer 7), both the tag and the calendar pop-up box appear in the very top of my screen. In other words, I can't use them, and therefore can't populate those fields because only the bottom of these pop-up boxes are visible. They are not at all accessible.