IRC (Internet Relay Chat) in late 1990 or early 1991. Got onsite reports and didn't have to wade through US government or commercial news censors, of what was happening during the first Gulf War. It was pretty clunky back then, but the greatest drawback was bandwidth. No fiber optics, wireless routers/modems, and dialup, if I remember right, topped out at about 1200 baud. Tied up phone lines, too. IRC is where a lot of today's netspeak (ur, LOL, gr8, etc.) originated because of that low bandwidth - time wasn't money, it was information gridlock.
I downloaded and paid for a copy of mIRC with the understanding that one payment was good for all future updates. Khalid lied. When he decided to stop making useful updates and people stopped using it, he wiped out the data base with all the paid customers. A crash a couple years ago made me download a new copy and that's when I discovered the crime. Now I stick with free stuff, and if the creator's start charging I find something else free.
Not because I'm really excessively cheap, but because I don't like paying premium prices for mediocre stuff. I prefer value for my money. And I hate subscriptions. Ugh.