Most of my gaming group live about an hour away from me, in Podunksville. I finally wrestled the first Saturday of every month away, so one night a month we play at my house. Well, as members of the group acquire more responsibility, we find it harder and harder for us to meet face to face. So we kicked around the idea of distance gaming and I went on the hunt to find some technologies that helps bring the table to the internet.
I have tried each of these applications, unless otherwise stated, and have provided as much information as possible to help anyone else out there decide whether they like it or not.

RPTools free apps
RPTools’ MapTool
RPTools have a suite of five open source, cross-platform (Java 5) applications at your disposal. Honestly, I cannot believe this stuff is free. Even the one app still in development, the CharTool has a very nice level of refinement. They offer the DiceTool, MapTool, TokenTool, InitTool, and CharTools (still in dev) on their site.
The MapTool is a client/server app which means you can either use it to host your own games or to connect to someone else’s. You drop in an image for your map or use a default background that can be tiled. You can pan/zoom the map as well as lay down a grid. Tokens can also be added to the map to represent PCs, NPCs, monsters (which are reall just hostile NPCs right?), treasure, obstacles, whatever. You can assign a few attributes to tokens like name, status, and if it gives off light. You can use the TokenTool to easily create slick looking tokens for the map. The MapTool also supports fog of war, drawing on the map, and a simple chat program with dice rolling functions. The DiceTool reads dice expressions (i.e. 1d10+2d6+4) that can be be saved to buttons and extended by using JavaScript. The InitTool helps a GM track initiative as well as character stats. Finally the CharTool is a character manager that can be used with any system but comes with pre-made configurations for D&D 3.5, Savage Worlds, and Heroes.
I definitely urge you to check out RPTools. Its free, works on any machine with Java 5, and if you are code savvy, can be extended by modifying the available source code.

NBOS' ScreenMonkey
NBOS’ ScreenMonkey
ScreenMonkey is from the same people that brings you Fractal Mapper, NBOS. ScreenMonkey requires that the GM be running on a Windows machine, but players can connect with any modern web browser. The full version costs $34.95 USD (and you only need one), but there is also a free Lite edition which comes without scripting, saving, and announcement capabilities.
I think the biggest selling points for this software is that you only need one copy, it is easy extendable by editing the HTML page players see as well as supporting the fairly robust VB Script. It has a powerful chat program, chat archives, and extendable minis. It supports initiative, fog-of-war, Fractal Mapper maps, sound (mp3 & wav), dice rolling, and map annotations. I have used this software a lot, myself.

Smiteworks' Fantasy Grounds II
Smiteworks’ Fantasy Grounds
Fantasy Grounds II is a pretty slick looking application, and probably is the most refined app out of the list. It is probably the closest to what DDI wants to be, but it just so happens you can use FGII today. However, Smiteworks wants to charge for both player and GM licenses at $23.95 and $39.95 USD respectively. It has a lot of DirectX, so this is Windows only.
FGII supports some nicely animated dice (color customizable) to roll, player handouts, maps, tokens, portraits, drawings, character sheets, and even rule book references. It has a very robust integrated chat client and supports the linking of resources. It has some sweet drawing utilities that even support pressure sensitive drawing tablets.
It has character sheets, combat tracker, and player turn seperation in the chat window. If you have the ca$h to spend, this might be the app for you.
Smiteworks also makes adventures ready to use with FGII.

d20Pro
d20 Pro
d20Pro is also very polished, I just wish my 30 day trial hadn’t expired before I really put it through the paces. It is available for $29.95 and everyone will need a copy (each copy can be both DM & player). There is a Windows version as well as a Mac/Linux version.
d20Pro has done a pretty good job at incorporating the d20 rule set. You can program attacks for monsters which is based upon their Hit Dice and Strength or Dexterity. Special ability templates and the four OGL spellcasting classes of cleric, druid, sorcerer, and wizard are all supported and extendable. Spell effects are tracked during play and the spells integrate with the special ability templates. Fog-of-war, grids, feats, skills, intiative, and saving throws are all supported. d20Pro has a dice roller, saveable game logs, a main chat and separate player to DM chats. You can even give monsters an inventory. All in all, it is a pretty solid application, if you are playing a d20 game.

B-grounds
Battlegrounds
Battlegrounds is a pretty decent virtual table top that I find very similar to FGII, but it works on both Windows and Mac (sorry Linux users). It has a dice roller, chat window, fog-o-war, zoom, grid snap, and supports .png which means you can have transparencies. It also has nifty token facing and label overlays. Battlegrounds is also coming out with a Wargame edition that will be suited to wargames. Battlegrounds comes in two flavors, GM or Player at $32.00 and $16.00 respectively.

OpenRPG
RPG Host’s OpenRPG
Open RPG has been around awhile (remember WebRPG?), and is the oldest of the open source solutions I am aware of. This application is cross-platform and available for the cheap price of free. It also has a decent sized community supporting it.
It has all the basics, map, miniatures, chat and dice. You can zoom, grid, and freehand draw on the map as well. The game tree is the most customizable aspect, allowing users to create custom character sheets and GM aids.

kLoOge Werks
kLoOge Werks
kLoOge Werks is a cross-platform (Java 5) digital gaming table that comes with two different licenses. A GM license costs $30.00 USD and the player license costs $15.00 USD, with bundle discounts.
I actually got a demo version of this at the first GenCon in Indy. It is fairly polished and includes a map with masking and fog-o-war, programmable dice, chat, spell shape templates, and a round-to-round event tracker.
It supports the big three image types (.jpg, .png, & .gif) as well as threatened areas, character sheet based dice expressions, animated gifs, audio support (.wav, .au, .mp3, .ogg), event based sound, facing, and health gauges.
Its pretty full featured, and definitely a contender. The GUI is pretty polished even if their website isn’t.

D&D Insider
D&DI’s Game Table
D&D Insider: This is the official platform for playing D&D 4e online and is available for a MMOesque monthly subscription of $14.95 USD, and its only available for Windows users. Most of us are aware that D&D Insider’s online tools are way behind schedule (and therefore over budget as well). After pulling the plug on their social network for gamers (Gleemax), Wizards of the Coast is focusing all their resources on developing what may be the best platform for playing 4th Edition D&D. While it hasn’t even reached beta testing yet, all the video demos of the software are very polished and professional. It gives you access to a Character Visualizer (make digital 3D mini of your d00d!), Dungeon Builder, Character Generator, Game Table, D&D Compendium (rules), and access to the online magazines Dragon & Dungeon.
Though I haven’t used it personally (who has?), from what I have seen, the Game Table interprets the rules for you, making movement/action available based upon your character (ex: highlights all the spaces you can enter and targets you threaten, only shows what your vision/light would allow).
While I was writing this, D&D I News published a post that gave a sitrep (situation report for the uninitiated) on DDI. Apparently, they offered a pricing structure so they can charge people for reading Dragon and Dungeon magazines. Check it out if you are interested.
Here are some other applications I have looked at, but not tried:
GC is still in active development, but has a beta version out. The beta has the basics, including an interactive map, dice roller, and chat, as well as map masking, ability to draw on the map, and hit point and initiative tracker. It is going for a fairly refined interface, so it requires a video card that supports Pixel Shader 2.0 and it requires XP or Vista. The app is available for FREE.
RPGtonight is browser based and you operate off their hosts (with space available for storing game info). It has a map with masking, chat window (which can be disabled if everyone is using voice), dice roller, and avatars. Its free and works with any OS that has a web browser.
Viewing dale uses your graphics card to present quickly updating maps. It has an integrated chat and dice application, but beyond the fancy graphics program, doesn’t offer much. I believe you only need one license ($45 USD) but it only works on Windows.
The Generic Roleplaying for Internet Players software is an IRC app published by the makers of Traveler RPG. It is basically just a layer you add onto IRC, much like mIRC if anyone is familiar with that. Finding, installing and using the software is somewhat cryptic, and it costs $35 USD. Also visit http://grip.2ya.com/ for more information.
It’s an online Paranoia rules infused app. I haven’t tried it, but its free and I think its programmed in Java, which should make it cross-platform.
This still in production software looks promising, it has the basics plus spell shape templates, lighting, masking, complex chat, and a combat tracker. Its Windows only and I’m not sure how much it will cost.
I can remember seeing this at GenCon last year. It is still in beta and appears to have all basics but ups the ante with video chat.
Simple online multiuser whiteboard with a chat box and dice. It looks to be browser based using Java and its free.
Looks like a very general online card, chess, boardgame app that must be used with Skype.
Listening to: Gothminster – Empire of Dark Salvation – Monsters
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