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If you want to be able to upgrade Askbot and still have your customizations, I would try using the custom extra context generators. They are not documented yet, but several view functions including the questions load extra template context, take a look at the source.

In that case I would probably create an additional table related to askbot_thread where I would store extra data. You could also patch the askbot's tables - but then you might need to fork askbot repo, but lose possibility of easier upgrades.