I loved 2008-2011 era the most probably, just loved the general "wild west" feel of internet back then, and blogspots, and the general look of sites (example: ferrarimurakami.blogspot.com)
it was a beautiful time when i first discovered the internet sometime around 2002... used to go on mofunzone or cartoon network and play games everyday for hours on end.
2000-2004 and 2010-2012
first one was when i discovered the internet as a child and it was legit magic
latter was social media without everybody trying to force their politic agenda down my throat
Probably 2005-2008. The internet wasn't as primitive as the early 2000s and we were passed using dial up, but was still moderately useful. You could still catch up on news, order things off the internet, etc
Instant messaging like AIM, YIM, MSN were still popular.
I also liked the YouTube layout during this era the most. The 5 star ratings & upvote/uptown system. I thought it was funny how if a comment got lots of downvotes it would hide the comment. Then when you opened it, it would feel like a surprise troll comment because you never knew what you were gonna see. I also liked how you could add "video responses" under videos.
Social media was popular mostly among teens & young adults and was not overexposed like today. The layout on SM like YouTube & Myspace gave you so much freedom to customize your personal pages and make them unique to you. The same with personal blogs.
I had a looot of fun in chatrooms just talking about music, games, and roasting people. And forums were still very popular. I prefer forums to more revealing SM like Instagram. When music leaked on the internet, it blew up and you'd have threads with pages for days. You also didn't have to worry about your fav celebrities exposing themselves as jackasses on SM all the time. I had lots of fun on Yahoo! Answers as well.
The late 2000s/early 2010s still had good internet but it was really just the beginning of the end. The internet/sm today has far too much influence on pop culture. In 2005-2008, the two were still relatively separated.
2006-2010: Club Penguin, Myspace, Miniclip, and xat.
When cod 4 had just released. It was the best thing on 360 and those were simpler times. Social media had not taken over so many pathetic lives.