Do I see a Louis Rossmann fan here?
I have no other Apple product, but I find it ridiculous that the cable has to have a chip in it to decide to allow it to function properly or not. I guess you have problems because of that. At worst you could try transferring them over Bluetooth (or WiFi with a help of an app) if everything else fails.
You should also add an option for "I'm using a Mac with whatever OS I wanna boot" because I can (and do) boot all of them when I need them. macOS for video editing, Linux for multiplatform stuff, and Windows for general usage.
Also, I must be very lucky, because I have no problems with my trash-picked 2011 13" MacBook Pro. I fixed the touch pad too, and it works perfectly. It is a fully upgraded model too, so this was a lucky find, considering it survived being in rain too.