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Upon further experimentation, I could only make it work by grouping by context.

If I use the setting at the bottom of my post above, then the tasks are all over the place... like almost randomly placed...

I even tried a different project from scratch with those same settings, just to make sure it was not some kind of file corruption.
I also trashed OF's preferences (the Plist), but it didn't help...

So did I understand the concept wrong in the first place?
Is the only way I can see my tasks in the same order as the contexts by grouping them? If so, why wouldn't it work without grouping and only sorting by context?

Thank you.