Maybe Amazon in 2000 wasn't so icky but there was also no free same day shipping. Apple II could be repaired without "special tools" but those machines were huge, heavy, mostly empty space, and gap and glass alignment was way worse. I wish I could say something smart about Windows 95 but I've worked hard to erase it from my memory, so I can't. :)
Electronics things, just in general, did a lot less in the past. With that comes good and bad.
Privacy is a trade-off and right now the general public doesn't place a high value on privacy so they're happy to trade it away for anything. Honestly I understand it. I'm convinced I'm going to get bombarded with marketing nonsense regardless so I might as well get something for it.