1/ Hard to top Chumley on my #1 (
). But, late 92/ early 93 my Dad bought me a Munton's ESB 'kit' as a birthday gift, which then consisted of two cans of hopped liquid extract and a packet of dry 'Yeast'. Today I would say the beer likely sucked, but damn if it wasn't good then. I was hooked.
2/ Trying to brew commercial caliber beer every time, if not better than most. Many of my friends and family think I do this every time - they're wrong. I'm getting closer, though.
3/ Plenty of mistakes - infected batches from poor sanitation early on, a couple of batches badly oxidized, mistakes in adding hops at the wrong time/amounts, etc. If you brew long enough there'll be plenty of stories like this.
4/ I don't go out quite as much now because there are a lot of very mediocre new breweries in the area, but I still have old standbys that I hit on occasion.
5/ Brewing can literally be as simple or as complicated as you choose to make it. Start out simple, read thoroughly first, and remember to enjoy it. If you're getting anxious and losing sight of the fun, you're doing it wrong.