Forgot to ever actually post the update. We've played twice now. Our session this last Friday was much better than the first. During the first, some glitch kept kicking me out during our second combat. Something weird to do with the "minis" we were using. Meaning the tiny little .jpgs of the monsters.
This time, we didn't have that problem. And to avoid any other problems with my wireless internet, I hooked straight into my modem instead. Having a large monitor (which I don't, I was using my tiny netbook pc) would be a plus, since during a combat you probably have 4 different windows up: chat, combat tracker, map and character sheet. I may buy a cheap flat screen off of Craigslist just for this.
After everyone gets used to the program, combat is a breeze. We were playing 4e D&D, but I assume that the mechanics are pretty much the same whatever system you're using. It comes with 3.5 D&D as a base, and there's a Savage Worlds version available for purchase pretty cheap.
Anyway, to attack, grab the dice off your character sheet (this has all your modifiers already accounted for) and release it over the monster you want to attack on the map, or over it's name in the combat tracker (an initative list that also lists the health status of all combatants). The dice rolls and the result is shown to everyone in the chat window. If you hit, grab your damage dice and release them over the monster and rolls the damage and applies it automatically. You can also add status effects etc in the same way. So it's pretty slick.
We used a voice chat program called Ventrilio as well as the chat box to communicate. I think it's popular with the MMORPG crowd. That was also super easy to use.