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We are observing same behavior. On restarting VS it resets the checkbox state as selected.
XVS 1.12.278.0 (b3acb09afda91828e5bd48308ac8e7433d30f330)
I have checked this issue with following builds:
Xamarin 188.8.131.52 (c376d19d2984310ff50a6e741e3e3e9ce4f920a5)
Visual Studio extension to enable development for Xamarin.iOS and Xamarin.Android
Now, "Notify about updates" selection is working properly. On un-selecting "Notify about updates", it does not reset on reopening VS.
Hence, Verifying this issue.