Oh boy, 23 years in Astronomy with many many highlights.
The first that comes to mind was back in the early days. I had my 10" Meade Starfinder set up in my surburban backyard and was looking for the Helix Nebula. I know...crazy!!!
Well I found it after a lot of searching and was so excited I ran inside and called my mate Grant...at about 3am
His parents were not impressed.
These days I focus 100% on outreach. My most memorable outreach experience was at Princess Margaret Hospital for Children in Perth. I had a small scope set up and was showing the kids Saturn, Moon, Jewel Box etc. A young boy came up to me as i was packing up and said that he'd been there for six weeks and this was the best thing that had happened to him so far. I'll never forget that.