I don't see any compelling reason to use in-app purchases in this
scenario. If the season's over, the app is probably uninstalled for
that subset of users who know how to uninstall and forgotten for the
rest.

Bringing out Fantasy Football app 2011 sounds like the right approach.
I wouldn't change your last app to free, just clearly label it 2010
and mention the more awesome 2011 app is available now. In fact, you
should probably just raise the price to $2010 as a tax on those who
don't read the title or description. Changing it to free will just
encourage more people to download it without reading the description,
and then commenting that the app is out of date, 1 star.

Hopefully, you have an optin newsletter for your current users, so you
can announce the new version and encourage them to comment on the 2010
version saying 'This is awesome, but the 2011 one is even better!'

Nathan

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