Thread: OF vs. Things
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I would say, you have the gist of it: Things uses tags heavily, relies on them. At this point OF does not have tags and you cannot assign a task to more than one context, although OF may support TAGS in a future version. And like you said, either approach will depend largely on your own personal system.

OF probably tries to be a bit stricter in following GTD principals.

Sometimes this works well, other times it seems like it works against you.