Well, talking about funny or frustrating moments in Roll20... The very first game I ran on Roll20 was in person. I have a group of friends from college that (prior to using Roll20) would meet once a year for a weekend of gaming. Someone has to GM (and more often than not, that someone is me) so I prepared a series of encounters, a plot, highlights from the last few thousand years of history, npcs, etc. The game dealt with a party who had become folk heroes and champions of the realm due to some prior event and were now the A-Team for the realm's king, sent to deal with issues. Pretty standard fare. The plot involved getting sent by the king to look into rumors in a duchy to the east, and the various goings on there. To get the ball rolling in situ, I went with an opening gambit (ala James Bond) where the party is on a walled keep that spans the only traversable gap in the northern mountain range preparing to receive an orc force that scouts said were headed for the walls. It started to diverge from there... the players really got into the defense role and devised various plans and strategies, turning what was supposed to be "a roving band of orcs dispatched by just the players" into "Helm's Deep". I had a big green page on Roll20 where I had drug in the PCs and the orcs, just a scoreboard sort of thing where only I could see it and track initiative and health and roll the attacks and such. As their plans got larger and larger, I kept having to resize the page and drag in more and more units, building Warhammer-esque squads on both sides. Eventually I probably had 800 tokens arrayed across a 200 x 200 page. With 5 players, on each of their turns they made an extra d20 roll adjusted by an appropriate stat to see how their various squads did that round (Fighter had warriors on the walls, Ranger had archers on the towers, Cleric had healers in the courtyard, Mage had squads with boiling oil, etc). That battle took us the entire weekend, with lots of little twists and turns and sub-engagements and an epic giant-growthed, roid-raging, hill giant towering above the keep smashing and such. We had a blast and never touched the prepared plot. The players decided to take the plunge into online gaming with Roll20 a that point. I asked them what the part would do now that the north had been defended, looking forward to running all my prepped plot down south in the kingdom... ...they unanimously decided to go north. 3 years later and we still haven't gone back to the kingdom. As an introduction to Roll20, it was a blast. Having set up Orcs as characters, it was trivial to build from a few orcs in a raiding party to a full on epic war machine rolling up to the keep. And the best part about having set up in Roll20 to run the local game, by the time those players had driven back to their homes (some 3 hours away or so), we played a short encounter with 3 of them that evening with almost no time needed to get rolling. (I think it took longer to get my less technical friend online than it took to jump into playing. =D)