For me one of the greatest times of freedom was during the life of Geocities. This was actually the only time I had a website, and I was in middle school. Sure, there was a lot less people on the Internet, but it was a very wild wild west atmosphere and I feel like a larger portion of the users created their own home pages than today. Malicious parties were not as widespread and powerful, and there was overall not so much control over everything. I was also using Napster at this time.
I've studied computer engineering and I've still had a hard time having the feeling / spirit of freedom and ease of contributing to the Internet as I did back then. Maybe it's because I'm not creative anymore, or because I'm too cheap to pay for or too disinterested in putting my content onto services, or because there's a lot more to worry about with running your own server, or because there's too much visibility/scrutiny/copyright enforcement. Doesn't have the same feeling of openness as back then.