I have an app published in the Windows Phone store for more than two years. So I started development on this app at Windows Phone 7 times where there was no In-App purchase available. Best-practice back then was to actually publish two separate apps, one Free version (most of the times ad-served) and a Pro app with some kind of Trial functionality.
In order to get both two different XAP packages I created two separate build configurations with different pre-build and post-build actions. So what the build does is:
As In-App purchase is out for so long and maintaining two different apps at the same time is time-consuming (although it's 100% same code with some free/trial/pro conditions) I would like to move away to just one app in the store that is free and contains In-App purchase to enable the Pro-features.
Now my questions are:
It's hard to answer your question - but here goes some resource - a friend of mine, once gave gave me a link to a very nice research made by Wesley De Bolster, described on his blog.
He described a method allowing to differentiate old paid users from new users - the main idea is that you get recipe with CurrentApp.GetAppReceiptAsync() and retrive the date of the purchase from it. After that you can compare the date of app's new version to the one obtained from the recipe. Then you can allow old users to use some features without buying IAP's. I haven't tested the procedure but seems to be a good idea.
Going back to your question, here is what I would do:
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