I think my first experience was around 1993 or 1994. I downloaded the 3.5" disks at the university and then uploaded onto my 386. No GUI, all command prompt. :).
Right around that time, too, I found some network cards and co-axial cables and 3-4 of us in the house put the cards in our computers and could see each other’s computer. Couldn’t do much else though. Hahahaha.
I recently found ground.news. it is an interesting news aggregator sight in that it combined multiple sources for each story. It doesn’t really answer some of your needs but for each story it shows you which sources are pay-walled and which ones aren’t.