I'm going to warn you in advance, there are some spoilers. Maybe not so much this post, but the following one for sure. I'll try to be vague where possible, but some of this is impossible to obscure ;)
I had expected up to 8 players and we wound up with 6, which means that we had a swarm of 18 peasants looking to brave Sailors on the Starless Sea to save their fellow villagers. Those numbers would suffice with some attrition.
The nice thing about using Roll20 within Google Hangouts is that you can incorporate the maps included with an adventure and make them the playing fields.
The Fog of War feature rocks. The one issue I have is that things like traps, secret doors, hidden stuff are on the map. I've learned the trick to keep most secret / concealed doors hidden, but the other stuff? Not so easy. It's one of the any reasons I appreciate the Purple Duck releases, as they generally include both a DM and a Players version of the map. Upload the players version and you are good to go. If only Goodman Games would follow the trend... hint hint.
Now, although I use Roll20 as our VTT, I don't use, or at least up to this point haven't use, tokens. I remember my days of playing weekly Fantasy Grounds 2 sessions, and always waiting for one or more players to catch up with the group. I've also found it to be a bit distracting at times.
I'm trying to think how the session would have looked with 18 peasants and a half dozen beastmen on the screen and cluttered comes to mind - as well as the confusion of players trying to keep track 3 PCs each with their tokens. We did okay just using the "ping" feature of the pointer.
I am open to using tokens in the future, as one of my players inquired about it and it may be fine to experiment with for a session or two. I just don't want the token pushing and the usual accompanying tactical mindset to take precedence over the immersion of the Theatre of the Mind. There may be a balance, and if so, we'll find it. If not, I've survived this long without tokens.
18 PCs meant that I couldnt keep track of them all, so I left that in the hands of the players. Next session, when we have out usual 6 PCs or so, I'll keep track on my side of HP and PC basics. It worked well last night, and everyone seemed to have a good time, even if I had to prod the players at one point about an item they had to avoid a total TPK. It seems the players had trouble tracking stuff on their side too ;)
As for avoiding the TPK? Even in a funnel you need survivors. This was the first DCC RPG session for most of my group. I wanted the funnel to be fun and exciting, not discouraging. Besides, I figured they'd get whittled down in the following encounter, but they proved me wrong.
Money - Though I'm told to think otherwise, I don't believe that D&D is just a game of going out to a dungeon or other lair, killing everything and bringing back...
4 hours ago