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 like #newsblur too. I have paid for it for years now (though it is free).
What I like best about it is that it caches the text and images of the site so I don't get all the ads etc.
Every year or so I go around looking at others but always go back.
I like start.me. It isn't something to download but it's a web page. The free service is a great start. I've been using it for years now
I wish there something like that for RSS feeds. That would be fantastic.
For news specifically, Google News and Ground.news both aggregate and cluster similar news articles.
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.