On the other other hand, Windows 3.1 has some upsides. Running Windows 3.1 is an experience, plus it's on DOS, and having a Windows 3.1 install on your laptop is cool/makes good art/conversations pieces. Vinyl would be interesting to listen to once or twice to show off to your friends, but it'd be more like something you'd set up once to see how it used to be done, then you'd go back to an iPod. Windows 3.1 is an experience, vinyl is a novelty.
I think the closest equivalent to the claim that vinyl is lossless would be that Windows 3.1 is efficient. Well... sure... if you squint hard enough and tune the definition of lossless/efficient properly, sure... but not in an actually relevant manner.
Windows 3.1 is on DOS, so it is lossless. There's no intermediary between any program and any other program. Everything runs in pure, unadulterated Ring 0, raw, unprocessed 16 bits.
That can be your opinion, but computer usage is a subjective experience and I'm entitled to my opinion as well. I find Windows 3.1 to be a superior computing experience; it has a charm and novelty about it that later Windows versions haven't been able to duplicate. I find the experience richer and more satisfying. Also, I like having to restart my computer and swap out physical floppy disks -- the tactile sensation and sound of disk access is much more pleasing than modern, silent, sterile SSDs.
While you are obviously exceedingly clever, you're funny inversion is BS. Vinyl isn't a novelty. It is a small but non-negligible market. In my anecdotal experience, myself and my friends have had record players and have been listening to and buying records for years. The "market" for Windows 3.1 machines in 2015 is microscopic and completely negligible.
