[Toadling]

Interesting idea, but I agree it sounds like a lot of work, especially for that kind of tight integration with other apps.

Personally, I would prefer something more flexible, more universal. For example, what if contexts had a notes field (similar to the one that already exists for projects and actions) that could contain text and attachments? Perhaps it could be accessed from the inspector? Then you could drag/paste in Address Book vcards, phone numbers, email addresses, URLs (IIRC, you can create URLs to initiate Skype calls), files, apps, or any other bits of information that you want associated with the context.

-Dennis