How about not talking past each other and declaring victory? The majority of software, prior to the internet, were necessarily optional. There were corporate lock-ins. These are not the software most people purchased/owned.

2000-2005, the biggest automatic updates that consumers had to deal with were Windows (Office, OS, etc) updates and games. Valve's Steam, which had come into prevalence (notably Counterstrike:Source), World of Warcraft, etc.

By 2008 (Google Chrome), automatic updates were common. I would say the ship had sailed by 2005. Yes, this is 1 full generation ago.

Yeah this guy has rose coloured glasses.

Remember when Java and MySQL weren't owned by Oracle?

I do.