Outside of dungeons and dragons itself I would say the best moment I've ever had was actually FINISHING a roleplay. It was pre-guild fall and on free and I was still adjusting too roleplaying this way so I downgraded myself to free. I ended up taking over the gm's spot more or less for my group and having free handed most of the stuff for my group. The roleplay was probably nowhere near consistent in it's writing but the mere fact that I spear headed a roleplay into the end game made me happy