Hi, John.
I don't have any solution for you.
I might be able to guess why context is missing from sort. If a task with more than one context is viewed with contexts grouped, the task will appear in more than one place. I often have this situation; a task might have a context for where I want to address it, for the customer involved, and for the tool I need. It would be difficult and confusing to make a single task appear in multiple locations in a sort. There is also a consideration when a context includes another context, I can't work it out right now as I don’t have access to Windows.
The most likely implementation of context sort would be an alphabetical sort of the contents of the Context field, which would mean that the task would essentially be sorted by the context listed first. In my example, if I looked for tasks for a certain customer I would miss this one as it would be sorted under its location. This seems the kind tool that could leave new users confused and frustrated, I would suggest not proceeding without a proposal to avoid this pitfall.
The suggestion to hide group headers has more promise. You could make a view that's confusing but it would be easy to understand what went wrong and put the headers back if needed.
If no one else objects I would suggest bringing this to Jira. As you have expressed concern about learning Jira, let me spell it out for you.
1. Using a large-screen device (tablet or PC) point your browser to
MyLifeOrganized.net/mloissues
2. Click on a bar at the top called something like "report mlo beta issue"
3. Fill out and submit the form.
That's all!
-Dwight
Mlo betazoid on Android sgn2