If copyright were shortened to 20 years as suggested, it would be legal to freely distribute copies of Windows 98 and Photoshop 5.0. I doubt that would make a dent in sales of Windows 10 or Creative Cloud. Newer versions of both would still be copyrighted, and there would be no obligation to release any unpublished source code.
Sure, but that's what projects like QEMU/DOSBox/other emulators and compatibility shims are for. There's so much abandonware out there, especially games that are stuck in licensing limbo that can't legally be acquired - and it's only going to get worse going forward as things like licensed middleware, soundtracks, etc. have been thrown into the mix with their own headaches.