Roleplaying used to be a bigger part of my life and I really miss it. There are a bunch of excuses I regularly use to explain away why I don't play that much anymore, but the main reason is pretty much what I've heard from a lot of other people - the gaming group I used to play with don't live nearby anymore and getting everyone together physically at the same time to play is difficult to impossible. The idea of using a virtual game table over the internet isn't new, and it appears there are lots of options for online roleplaying. The hard part is settling on one that will work for everyone. The solution has to be easy to install and use, preferably cheap or free.
RPtools.net offers a robust suite of free tools (including MapTool which is the main virtual game table program) and d20pro is a commercial application which offers pretty much the same functionality - its available on a 30 day free trial. Both are cross-platform capable which is a requirement since I use Linux and OSX primarily and doubtless I will have friends that run Windows that will want to play. Both seem to provide the same set of features and functions, though d20pro is, as its name suggests primarily geared for games based on the d20 system. Since I've been playing D&D3.5 with the kids and would probably want to continue that game online thats not an issue, but I've also given thought to running Warhammer FRP instead and using MapTool might make that easier since its not so tied to d20. MapTool is easy enough to navigate around, and theres a great set of video tutorials made by one of the MapTool community members to get you started, but extending it through automation is done through the use of Macros which means a learning curve of some unknown shape. d20pro is supposed to be easier to use to automate tasks.
The fact that MapTool is free is a compelling reason to choose it since without knowing the level of interest in playing online in the first place, putting any monetary requirement on it might be a deal killer. So far I've managed to install and create an encounter map for the as-yet-unscheduled online D&D game though I haven't gotten as far as creating sightlines and populating the map with baddies as yet.
Playing online also requires voice communication. This has traditionally been more difficult to do easily for free. WoW (and first person shooter) players have been using Ventrillo and TeamSpeak for a long time, though mumble is a free and open source solution that has worked for me once or twice. It seems that it should be pretty easy to get everyone on a group voice chat in google talk though at last check group voice chat in Google is currently a work in process. Skype is another solution. Any others out there that are free and easy?