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Timestamping is necessary if you wan't to be able to continue to update the XAP, even when your certificate has expired.
When installing the application, the user will still get the warning that the source isn't trusted.
He generally, avoids news and spends his time writing guides and tutorials which add value to the web.
To get Windows to trust your code (in my case a Silverlight Out-of-Browser XAP file), you need to sign it with a certificate.
With a Silverlight OOB app, this makes the difference when installing between seeing this: or this: Also, trusted applications can automatically update themselves (when adding the necessary code of course) while untrusted ones can't.
This is a moment of rejoice for the owners of devices having no expansion slots (like Lumia 1020, 925, 920; etc) as now even they can enjoy downloading apps to PC and then install over to the phone.
This is also helpful if you have multiple WP devices at your home and want to install the same app to all or them, or share the apps with a friend who has no data connection. With Windows Phone 8.1, there is no limitation about where you place the downloaded XAP/APPX file.