I rewrote the whole app and users that had the app with some CoreData data already there may experience problems with the new update. How can I tell the app store that when the user updates the app, the previous app needs to be deleted completly and install the new one update?
I believe that the new version is overlaid on the old version. I know that NSUserDefaults and all local files are preserved; I assume Core Data would be also.
So regarding your question - You can't. You could have the new version detect the presence of the Core Data and inform the user what they need to do to successfully update. But much better would be to get the new version of the app to handle the issue silently. An alternative is to first create a mid version update to the old app that manipulates the core data such that the new version can handle the core data from the mid version. Launch the mid version and wait two or three weeks before launching the new version.