I started playing right before my first kid was born - it was something to help me stay awake and i really enjoyed the custom content and boxing to overcome challenges and i was really bored with classic. I have come back to the game 3 times in the last 9 years because I miss the way that I can approach the content and never run out of things to do. Working my 2 groups through tier 2 currently.
My favorite fight/achievement at the time was taking down Nagafen with a SK/BRD/CLR way back in the day. Not exactly hard now but it was a rush back then. I immediately went after Vox because I didnt read the wiki on world bosses.
really the first time trying out each tier has been a fun adventure, i am grateful that the exp can be recovered quickly.
Also - really enjoyed Killing AoW with the now 8 year old on his warrior as part of my raid.