I can't even update to iOS 7 on my iPod Touch 4th gen, which means I can't get the new version of Remote, update a dozen apps I already have, or get a number of potentially useful newly released "iOS 7 or later" apps.
Windows, Mac, it doesn't matter - as time marches on you will eventually be disappointed unless you're in the camp that routinely updates hardware every 3 or 4 years.
Steve