Apple was on the ropes in 1999!
Classic MacOS never had an entirely reliable network stack for browsing the web but hey, they had a GUI running in 128k of RAM in 1984. Not to say that macs didn't have their charms during the .com bubble but it wasn't until Mac OS X came out in 2001 that a mac was a purchase that made sense.
The network stack was fine (they licensed the same STREAMS implementation also used in AIX, UnixWare, VxWorks, etc) - it was everything else around it (cooperative multitasking, no virtual memory, no memory protection) that was a house of sand.
The iBook also started at over $3,000 adjusted for inflation ($1,599 in 1999).
Were you actually a Mac user? The initial release of OS X was quite inferior to OS 9--it was an incredible proof of concept and perfect developer target, but for an end user, not so much.
I've been in computer labs full of Mac OS 8/9 machines happily browsing the internet so I'm not sure what your claim about "unreliable network stack" is referencing. Unless you mean "a crash requires a reboot" which was true, but also often true for Windows 95/98 as well!