New game, playtesting several interesting ideas

Recently started a new campaign, and the more I think about all the differences from what I'm used to, the more I feel like documenting it. For one thing, this will be the first full campaign I've ever been DM for. But there are many other factors at play.

-The game is gestalt, something I've never done before. It will be a struggle to figure out appropriate challenges, though I did limit it to a single class each side and only one prestige class total.

-The party is all evil, with an ultimate goal to destroy existence. Hopefully their shared religion will keep them together.

-Rotating DM. I'm in charge, but all the players will take turns at the helm, and each respective DM runs his character even while controlling the action.

-The game is being played online in a chat room. I've done this before, but it's always a struggle to handle tactical positioning.

-Despite gestalt, we have no true arcanist (just a bard who's switching to Warchanter ASAP) and no dedicated tank. What we do have is two divine casters, two super stealthy characters, and every single person with ToB maneuvers and a recovery mechanic for them. We basically have no super-powered cannons, but between healing and maneuvers can literally fight all day. The first session saw 5 combats (total of 25 enemies), and the party still had barely cut into its daily reserves.

The party of "heroes," listed below. Started at level 3.


The funniest moment of the first session:


Tomorrow Dolorito's player will be running the dungeon, we'll see how that goes. It'll be fun for me to go all out with my character this time, no need to worry about "the DMPC overshadowing the others."