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We've always felt that our customers shouldn't have to buy the seasons over and over again, so we always try to help you transfer the seasons from one version to the next. Unfortunately, Apple doesn't make it easy, but we publish instructions for doing that, and I expect we'll be able to do the same again next year. (It involves using a 3rd party utility so you can see your device's file structure, something that Apple tries to hide.)
So, you should be able to buy all the seasons in iOOTP 2014 and have them available in next year's version. Just ask when the time comes, if you don't see instructions on this forum. Thanks.
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