On the gripping hand, if you’re trying to connect an older external device, you’re more likely to get it working eventually under Linux (which usually keeps device drivers until they bit-rot out of the kernel tree) than Windows (whose drivers are version-specific and only get ported forward if the manufacturer thinks there’s money in it). Six of one, half-a-dozen of the other, as far as I’m concerned, and device setup is a thing you should only have to do rarely anyway.
Not my experience at all—I have stuff 20+ years old that’s still in working order. Maybe you’re particularly hard on your peripherals.