D&D Over Skype

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Alright. I suppose this is also an introduction thread for myself. So, if you will, allow me to get that out of the way first hand. 

I'm a fresh D&D player with a deep-rooted interest in the game, but not a lot of people who live nearby that are really too interested in playing. I've never been able to really finish a session as most of my friends tend to get bored after the 'lengthy' or 'complicated' character creation. 

I live in Virginia Beach, I've got a love for almost anything Sci-Fi and Fantasy, and I have an insatiable hunger for Dr. Pepper and Taco Bell.

To the topic at hand.

The friends that do share a common interest in Dungeons and Dragons tend to live states away, if not further. We're always trying to find new things to do to pass the time whenever our schedules permit a skype call or a quick online game. The problem is that online video games are becoming much less interesting and our avenues for creativity and gaming have recently come up short. 

Has anyone had a successful time playing D&D over Skype and if so, how did you get around the distance barrier? Is there a surefire, if not creative, way to have a fun and successful session with friends playing a table-top game minus the table? Are there any tips or advice for playing with long-distance friends, and what's a good starting point as far as books, manuals, and pregen dungeons for beginners like myself?
Skype is used by many people for online games, but mostly people use something like Maptools or GameTable as well, which are applications that  create a grid for combat, etc.

By the way, I share that thirst for Dr. Pepper!
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As Corran said.

Skype is great for allowing the group to talk to each other, but I don't think it would work at all well for showing things to each other - whether you're using a full battle grid, or doing mind's-eye and occasionally want to show a sketch to someone else to see if you agree on where things are.

(By the way, Skype is not the only option for that function.)

GameTable is what the group I'm currently in uses. We have people in two non-adjacent US states, Ontario, Netherlands, and Colombia. Yep, three continents.

We also use Hamachi, which is a public free-for-small-groups VPN (Virtual Private Network) package. This lets our computers talk to each other as if we were all on one local network with no firewalls between us. Without that, the DM would probably have to go into his firewall and do some special configuration, and then communicate his IP address (which could change frequently) to the rest of the group. With it, everything just works and the Hamachi software tells us the IP addresses of the other devices.
"The world does not work the way you have been taught it does. We are not real as such; we exist within The Story. Unfortunately for you, you have inherited a condition from your mother known as Primary Protagonist Syndrome, which means The Story is interested in you. It will find you, and if you are not ready for the narrative strands it will throw at you..." - from Footloose
@Corran: Thanks for the tip about MapTools and Game Table, I'll have to look into those then! 

And who can beat the call of the siren that is Dr. Pepper??

@warrl:  Ah, yes. Hamachi. Typically I use it for getting around having to purchase multiple copies of games when I'm feeling nostalgic. Like the old days with Star Craft or Command and Conquer, where playing LAN games with only one disk was doable. But other than that, I haven't really explored too much into Hamachi's.

And the multiple continents thing; that's insane. I have a couple of friends overseas and several all around the United States, so I know how that goes. The biggest thing is juggling time zones.  

I've looked into TeamSpeak and other programs as far as being able to broadcast voice and I know there are several internet based chatrooms that come packaged with dieroll commands, so that does help in some cases. If only Skype had the dieroll command! It's literally the only thing it's missing.

And yes, to be honest, we usually play using the mind's eye. Since our group is kinda small, it typically works. But I can understand how- especially in late-game or in sessions with multiple encounters- using a game mat or battle grid would come in handy.

At any rate, thank you for the hasty responses, both to Carran and Warrl; I got caught up with other things, else I would have surely responded sooner! 
I and both my D&D and WoD game groups have played over Skype, sometimes with the addition of an IRC channel for things that can't be done over the voice chat, and it actually can work out relatively well, depending on a few things.

Biggest factor is, do you all have the requisite books?  If not, then it might be difficult to game at all, because only one person would have the requisite knowledge to actually get/keep the game moving.

Next, do you trust your friends to all roll their own dice on the honor system, or do you think they might cheat?  Because if it's the latter, or even if you just want everyone to be able to see what is rolled, then you may have to use some sort of virtual dice roller.  We used one that could be loaded into our IRC channel for our WoD game, which meant that all we had to do was type in the dice pool amount, and it rolled for us, displaying the numbers.

Third, do you think you need to see people's physical reactions to things, their gestures, etc.?  Then there's the problem that you have to (last I checked) pay for group video chat on Skype.  This may mean paying, or simply investing in a different chat program.

And of course, there's the whole maps versus free-form for combat.  Some people necessitate having a mat with exact delineation of who is where, other people don't care so much, and can work without.  This really depends on consensus between you and your friends.

So yes, a Skype-based D&D game is plausible.  It just entails a little planning before the first session.  Figure out what you need, and who is in charge of getting/doing things before you go throwing yourself into it.  I personally recommend having access to a program like Trillian, which has all the requisite connections (Skype, IRC, various chats) in one convenient place, though you can manage it with just Skype if you find you don't need dice rollers and such in addition to it.
Elendae, you're right on all counts there. I'll be honest, we've been playing with the- I want to say- 2e AD&D books. The biggest thing about seeing each other through Skype is the payment. I do know that there are pages like tinychat and of course that oovoo program, though I typically don't use them as I'm less familiar and less trusting and from what I've seen the quality through those alternatives tend to be poor, anyway.

Thanks to the previous aid, I checked out both GameTable and Maptools and was honestly impressed.  I think my long-distance D&D experience will be a good one thanks to the help from the D&D community. My next biggest thing, though, is should I convince my companions to purchase the 4e books or wait until D&Dn comes out? I know it's in playtest, right now, and I've done a little bit of playing around with the playtest packet; personally I like the new character sheets and the character creation seems to be a bit more tailored for both amateurs and veterans.

So would it be better to buy the 4e books and convert to that or keep playing with the 2e books and wait until D&Dn?
I played a maptools/skype game for over a year and it worked alright. Skype can be finnicky if you don't have a solid internet connection. But, for the most part, 90% of our technical problems came from MapTools. So if you have a good map program (or play Theater of the Mind) skype can work quite well.

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I play D&D on Skype all the time (as a DM) with no Maptools or other aids. It really depends on the preferences of your players.

Our standard format is this; I DM, and I have a couple of players live on my end of the Skype call who sit right at the table with me. The other end of the Skype call is a couple of my friends in Vancouver, who have hooked a laptop up to their HD TV and have no issues seeing the game table/maps and miniatures.

I simply move my laptop on my end when I need to narrate things and move the laptop back when its time for combat so they can see the tiles or maps. Because I wear a head-mic I never have to worry about the players hearing me.

From what my freinds tell me, they can see the whole game table with no issues. I also use 3D tiles when I can to avoid overlapping perspective on the far end of the table.

It works perfect for us! 
I use Teamspeak 3. 

And for a game table I use Maptools.  

Then I use Obsidian Portal for a game Wiki.

Gimp is a free graphics program I use to edit characters for Maptools.

And I learned how to use Maptools and Gimp via youtube tutorials.  

I also posted the tips that helped me in the Dark Sun thread in my signature along with a link to some maps I made.

 I want a system where players don't have to pick between mechanics and roleplaying. I hope 5E fails asap so a better system can be made asap.

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My group has a player in Maryland that we play with (the rest of us are in Virginia) and we use Skype.  We just mounted a webcam on a tripod so he can see our table, with the maps, minis etc, and it works pretty well.
I've been hardpressed at work, but I'm still around! Just trying to manage my time a little; I know I have zero time and I'm talking about D&D? Madness. 

But thank you all for the tips and advice and I've looked into everything. I downloaded MapTools as well as a couple other peripherals just to test things out and I'm working on my setup. But again, thank you all and I hope I get the time to really get my hands dirty with the game sooner rather than later!
Maptools is extremely powerful but also extremely complex both internally and to fully configure for your game and characters. The complexity increases the risk of bugs.

If it seems a bit too much, look at GameTable. Much less powerful... and much simpler. 
"The world does not work the way you have been taught it does. We are not real as such; we exist within The Story. Unfortunately for you, you have inherited a condition from your mother known as Primary Protagonist Syndrome, which means The Story is interested in you. It will find you, and if you are not ready for the narrative strands it will throw at you..." - from Footloose
Yes, I've noticed some of the bugs with the "Tools" set. Mainly the character tools as I can't seem to edit pretty much anything, so there's that. I'll be checking out GameTable sooner or later.

Of course with the idea of Skype D&D on the mind, I'm looking to join a group once I get my hands on- at the very least- the red box as I haven't any 4e books, though I'm willing to learn even if by word of mouth.
i actually found maptools to be really easy to setup and build on, there are already alot of preset macros and campaing settings/properties for 4e.  We have macros that set initiative table, add/subscract hp, calculate surges, healing, etc... it speed up things quite alot.  Also the line of sight/fog of war works great too.
I play three types of games:

1. All of us in the same room sitting around a table.

2. All of us on a computer playing on line, using RPG MapTools (www.rptools.net/index.php?page=maptool) for the map and "minis" and TeamSpeak (www.teamspeak.com/?page=teamspeak3) for communication.

3. Some of us in the same room sitting around a table and some of us skyping (or iChat or FaceTime) in through a webcam.

All are quite successful. The best experience is with all of us sitting around a table, but, like you, I have farflung friends that I enjoy playing with, so the other options really open up possibilities for playing together.

We find scheduling, no matter which way we are going to play, is the most challenging aspect of playing D&D now that we are all "responsible" adults.
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