This topic will be all about how to play DnD over the net from your home over the interwebz (hence the underwear topic).
The hardware you will need will be a computer (duh!), a headset with mic and headphones. Here is the one I use.
The software you will need is a voice chat program that supports a conference call feature like Skype, Ventrilo or the like. You will also need the all important virtual game table. There are plenty out there, some free and some not. I have found that, for the modest price of FREE, you can't find anything better than Maptool (located at www.RPTools.net).
I won't be walking you through the setup of these programs as any voice chat program is fairly self explanitory. However, I will be talking about Maptool a little.
Maptool is an EXTREMELY versatile game table that can support just about any game you want to play, no matter the core system.
Building maps in Maptools is fairly simple, if a little time consuming. This is where I spend at least 1/2 of the initial campaign setup time for my games. There are plenty of sites out there that have premade maps from the user community, so if you stick to the official DnD adventure modules, that will save you a lot of map making time as someone else has probably already created the maps and your only task is to input them into your campaign and set up fog of war and vision blocking.
Maptools also has the added benefit of being able to load the campaign files someone else has created. For instance, I can make a maptool campaign, send the campaign files to you and you can load it up and play it. On this occasion, loading up someone elses campaign file saves you a metric ton of time. Again, if you stick to the official DnD modules, there is a good chance you can do this.
See the screenshot from an old campaign of mine:
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As you can see, my merry band of foolhardy adventurers are about to be eaten by a black dragon....should be fun. On the upper right hand side of the screen are my paladin's macros for attacks, skill usage, etc. The lower right are my macros (As the DM) for damaging monsters, players, applying various states (stunned, dazed, etc) and controlling most other aspects of the game.
Maptools macro system will allow you to automate just about every function/action your game needs. It only depends on how much time you want to spend setting up the program to suit your personal needs. On average, I spend probably 20-30 hours setting up the average DnD 4e campaign module and another 2ish hours every time characters gain levels and new feats/powers. Beyond that time, it's extremely easy to jump in as the DM anytime and play. There is no need to get out maps, mini's dice or anything else. There's also no need to drive over to a friends house with $20 worth of snacks in tow. Bonus!
Another good point about Maptools is the fact that there are already many frameworks developed by the user community for various game systems that will allow for a quicker setup of your campaigns/macros from the start.
The user community is also EXTREMELY active and helpful! I have never had a question I have posted go unanswered for more than 24 hours....ever. There are regular updates to the program to implement new features and squash bugs. Overall, it's the best, most well supported freeware application I have ever seen.
There are many video tutorials that will get you started and more tutorials and FAQs going up all the time. Over all, it has a learning curve, but one that is as simple or complex as you want to make your adventures. If you are like me, you will start out with macros and look something like [d20 + Weapon1Attack] and end up with how mine look today which is about 1/2 a page of code whose output looks identical to the DnD Player Handook power boxes. See this screenshot: (P.S. I love how I rolled a fumble on this attack. That is totally my Paladin player's luck. :)
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That's all for now.