I remember our biggest issue being IP addresses. We had no router, or expertise, so we were at the whims of automatic addresses (254.x... as far as I recall?). Good times.
There was always someone who would just be totally unable to connect with someone else.
The idea was specified in 2005, and there's a related question about Windows using these addresses in 2011 [1]. I haven't tried to find older evidence.
[1] https://superuser.com/questions/238625/why-is-windows-defaul...
"Microsoft Windows 98 (and later) and Mac OS 8.5 (and later) already support this capability."
And https://www.techrepublic.com/forums/discussions/win-98-fails...
It is amazing to think how much IPv4 and IPv6 "just work" in comparison.
That said my first LAN party was 1996 and we were running Windows 95 by that point, which probably helped.
No, I realy don't miss those times :-)