I think the coolest time was probably right after the original release, when money was incredibly rare and something was happening all the time. There were no silly jobs like bread baking and pearl diving that required absolutely no investment. Stefan held soccer tournaments, one of which 'my' team almost won, and I still think that Stefan got something wrong with the score
I also liked when the kingdoms were first created. It was not staff who did that, but the players themselves came up with everything.