I agree that there will be cases where you will only want one location for a given context. What I'd like to see one of two options.
Option 1: Allow me to edit contexts on my Mac like I can on my iPhone so I can add multiple lat/long coords for a locations (e.g. 'lat:long1' OR 'lat:long2' OR 'lat:long3') or multiple addresses. This will be ideal because then I can do more complex edits with a full keyboard and mouse. However, this may get too complex if you wanted to add multiple addresses or Contacts to a given Context. I've already sent a request for the ability to edit Context properties via the feedback button under help.
Option 2: If a parent context does not have any location information associated with itself, then use information from child contexts. This gives me the flexibility to assign an action to a general context that can be done at multiple locations or assign an action to a specific child context where it needs to be accomplished at a specific location. I've already sent a request for this one too.
In both cases the method you enter your context will dictate whether or not it is a single location context or a multi location context. Option 2 I believe is the better choice because it allows a person to more easily create this type of relationship right from their iPhone.
Love to hear any thought or comments.