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[what about a ]context for purchases requiring a car? Could such a context require trips to 7 or 8 stores? ... Is anyone on this forum going to argue that you should go to the stores without consideration of where they are
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This, I think, is a better example to talk about trying to get to the bottom of what you want.
First, I think you would want to assume that multiple items in the list of 7-8 things are equally available - i.e. the dependencies are all open and there isn't any Project level priorities. Otherwise, your Project level dependencies would communicate what is really available for you to choose between.
This example in particular is also interesting because OF iPhone already has a mechanism to "sort" context based on location. If you've assigned location information to those 7-8 stores, then OF iPhone can show you that list sorted by distance giving you the closest store first. It basically creates a sorted route for you using distance. At each location, it would re-sort the list.
So, you could consider this location based scheme an acknowledgement that Omni sees some value in being able to sort Context.
A manual sort might enable you to dynamically sort that list based on something OF doesn't know anything about - for instance on a Sunday, several of those stores might not be open or might not be open until 11, 12 or 1pm. Something that might feel ridiculous to record in planning mode - or ridiculous to think that OF would have a place to record such information.
Having said all that, let me praise you on being able to hit 7-8 stores in one errand run. You are the Errand Master! :-) I'm lucky to actually get to 2 stores and actually find what I need on a given errand run. (sorry, just poking fun... not meaning to detract from this better example)