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So, I recently moved to Norwalk, CT from a small town in Upstate NY. A lot of my gaming friends are still in NY, and I was kicking around the idea of getting Skype and have them control the board for games like Runebound, as I don't actively need to have my card and guy in front of me (they have my copy of the game) or using my copy of Smallworld while they use their own copy to have equal setups on each side of the computer to play. Similar style for Aye, Dark Overlord where I have a pile of cards to play and they and other friends use their pile. Of course, I could always be the overlord and not need any cards (they can pass out their own withering looks), but that would get boring. Anybody have practice Skyping games and how well does it work? Does it just get frustrating? Thanks.

I've done it with Vassal. Never with a physical board.

I play D&D over skype and that works great.
We use dice rolling lobbies and a page called cosketch to add in maps and images.

I can't see it being any different for boardgames. Maybe have webcams set up for the boards so everyone can see?

As someone who can enjoy the game aspect and modeling aspect separately (though I like them both), I've played a lot of games over VASSAL. It's a bit of a different experience - movement is tighter and faster due to the computer interface, but things like LOS and cover are more abstract - but it's a lot of fun especially when there's not a lot of opponents in the area.

Never done anything over skype though...

Depending on the game you could try Roll20 as well, in the same vein as Vassal. Roll20 even has integrated voice and video. There is some setup required initially to figure out what art and stuff you'd need, but they have dice rolling, line of sight measuring, movement, etc.

It was originally designed for D&D, but anything with a grid board could probably be cludged in.