Note: This is the 3rd part in a 4 part series about RPGing over the internet. You can read part 1 here and part 2 here.
Let's take a quick inventory of where we are. You decided to run or play RPGs over the internet. You've pulled together a group. Now you need to decide what medium to use to run your game. I'm going to run over play by post, chat, and various online tabletop programs with a bulldozer to see what turds and diamonds pop up. And away we go!
1. Play by post (pbp)
I'm going to preface this with a warning. I dislike play by post. I have not had a good experience using the pbp medium for RPGs. Ever. I'll still try to give it a fair shake on the pros and cons. Most likely I will fail, but here goes anyways. The good part about pbp is the convenience. Since there's no scheduled game time it is much easier to attract a group of players who will commit to updating on a regular basis. It's much easier to participate in multiple pbp games because of that same convenience. That's it as far as good points. On to the bad. Pbp games suffer from a unique problem. A player can leave the game or forget about it and not only may no one know about it for several weeks, but it can cause the game to come to a complete stop. Unless there is another method of contacting the absent player besides the forum you won't know if they've left the game, forgotten, or had something come up. It can kill the game if the DM doesn't step in and skip their turn within a reasonable amount of time. Pbp games additionally suffer from being unsuited to turn-based game structure. The more a RPG mechanics care about who does what in what order, the more pbp games grind to a halt when using that particular system. I don't recommend pbp games, but again I'm biased. I have heard anecdotes about successful pbp games. It may be you don't have any other options. Perhaps your experience with pbp will be better than mine.
It's possible you recruited your group entirely from chat. This makes setup quick. Simply create a new room and invite all your players to join. The downside to chat is similar to pbp, but not as debilitating. People can disappear off chat without warning and you won't know if they're gone for good or not. The easiest way to deal with this is deadlines. For example, I give players 15-30 minutes to show up after the official start time of the game. If I have enough (3 or more) by then I run the game. If not, I cancel the game for that session. This way a single missing player only cuts a little bit of game time. I start looking for a replacement if a player doesn't show up for 5-6 sessions in a row and they're not in my "core". Chat games can have issues if you're running a highly tactical system (4e D&D) without visual aids. Even with visual aids it is a slow process. I recommend running rules light or medium systems for a chat only game. You will need a dice roller if you don't want your players rolling meatspace dice. Dice rollers are easy to find, and some RPG specific chats even have dice rollers that can be invited to your private game room. The big upside to chat games is the technology is simple to set up and the downsides are easy to overcome. I started my online RPGing running chat only games. I recommend chat only games as a starting point for anyone looking to run tabletop games over the internet.
3. Online Tabletop Programs
You're not the only geeky person out there who wanted to play RPGs with people over the internet. Some of these geeky people got together and built programs to create a tabletop experience over the internet. First, I'm going to give you an overview of pros and cons that all online tabletop programs share. Then I'll give you a list of online tabletop programs and recommendations. The downside to online tabletop programs is the technology setup. Hands down, online tabletops require the most tech knowledge and time investment of all the RPG over the internet mediums. Hosting the server for these programs can be a nightmare. Your server can stop working mid-game. Learning the ins and outs of the program can take weeks or even months depending on your dedication. The advantage to working through the tech stuff is a near replica of your tabletop. Maps, minis, chat, dice rolls all of these take place in real time. It's very shiny and adds a lot to the game. I don't recommend using an online tabletop program on your first game. You'll have enough stress from wrangling players and prepping. You don't want to compound that with a technology failure. Once you have the experience of running online, then takes you steps into finding a tabletop program you like. On to the online tabletop programs.
ScreenMonkey(http://www.nbos.com/products/screenmonkey/screenmonkey.htm): Pay software that has a trial/demo version. I found screenmonkey to have speed issues, even on strong internet connections. This seems to stem from the fact that the clients all connect over a web java interface. While this does mean anyone with a web browser can connect to your server it causes slow downs and server/client sync issues. Unless you have an environment where your players refuse to download any software to their computer I don't recommend this one.
OpenRPG(http://www.rpgobjects.com/index.php?c=orpg): Free software with pay for modules and maps. This tool is fairly comprehensive in its offerings tool wise. The downside is it is not really in development anymore and only supports windows. If you have mac users in your group they are out of luck. If you rely heavily on modules for your DMing and don't mind paying for them this is a decent choice.
GameTable(http://gametableproj.sourceforge.net/): Free software. This tool is quite barebones. It has chat, a dice roller, minimal maps and customization. The good part is there isn't much to learn outside of the basics that come with all online tabletop programs. The bad part is there's not much room to customize to tailor to your game. I recommend this one if you're looking for a simple program.
Maptools(http://rptools.net/): Free software. Runs on java so any device that can run java can install the client and run it. From my experience this is the best supported, highest feature online tabletop out there. It is the photoshop of online tabletop programs. If you want to use it for its basics the learning curve isn't steep. If you want to dive in deep the curve is steeper, but it is matched by the customization you can obtain. The same site provides other tools for managing your game, but none are required to run. Except token tool. If you're not using tokentool you need to have your head examined. One cool part is your players can gain value from maptools even if you choose not to dig in deep. I personally don't use the macros, but my players do. Maptools is what I use for my games and I recommend it for anyone who wants a deeply customizable online tabletop program.
My final online RPG medium recommendations. If you're new to the online RPG experience, try out a chat only game backed up by a dice roller. This will give you a feel for how online tabletop games flow. Then give online tabletop programs a shot when you're ready to step out of your comfort zone. Next time I'll cover long-term questions and address the issue of burnout.
Art from GIS for iphone dice