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Well, at this time (AFAIK), none of the Apple online Stores (Mac or iTunes) has a mechanism for a paying update.
To make a user pay again, it must be a newly submitted app and I have not heard yet of a company going this way.
I contribute to an app that is sold on the MAS and the main developper confirmed me that.

Can anyone confirm ? Maybe the Omnigroup can can jump on this and clarify it for anyone to know ? Maybe OmniFocus 2 will be released as a new app on the MAS ?

That is my main area of concern to be honest with that bundle identifier problem again.

Thanks !