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Yes, OF is not going to remind you when you’re talking with Bob that when you are at the hardware store, you are going to buy something for Bob. I think the uncomplicated OF view is that either the task is to ask Bob about something that you are going to buy for him (in which case, the Bob context, obv.) or the task is that you are buying something that you have no further need to discuss at the hardware store (errands context).

But it is entirely possible that that doesn’t make sense for you, in which case, maybe Things is better. I’m personally much more of a fan of forums where, if I’ve responded to people’s requests for help, that they just say thank you and either try it or don’t try it, but don’t then argue about how I’m wrong.