[Brian]

I'd recommend a due date of Sunday or Monday on the "Buy Milk" action, which would then be assigned to a "grocery store" context.

I can see using a weekend context for things that could *only* be done on the weekend, versus things that *might* get done on the weekend.

That's one common thread I see in requests for tags - the intent is to make sure that an action is visible in all possible scenarios where it might possibly be relevant. That makes sense, but a list of things I may be able to do requires me to think and make more decisions when I look at it.

By contrast, OmniFocus tries to make sure that when you're looking at the list for a context, it's showing you the things that you couldn't get done any other way. Look at the list, do the things, move on to the next list.

OmniFocus wants to give you shorter lists that are more signal and less noise, in other words.