Video calls? Skype initial release was in 2003. Consumer OS with server-grade kernel? Windows XP first release was in 2008. USB thumb drives? Windows 98 didn't have drivers for them, so they came bundles with CD with drivers? Web browsers? Firefox initial release was in 2002, much hated IE6 - in 2001. In 90s you had IE5 - I doubt it was much better than IE6.
Skype's big innovation was its ability to work in NAT-to-NAT situations, not anything to do with its actual calling functionality. People were video chatting even way back in the mid '90s: https://www.sattlers.org/mickey/CU-SeeMe/internetTVwithCUSee...
The web made for IE5/Netscape 4 was much better than the current mess we have now. Websites were designed for the people reading them, rather than for analytics.
Yes, I deliberately tried to exclude the NT family by mentioning "consumer OS" :) BTW, how was Windows 2000 in terms of software (read games) compatibility?