I've selected MapTool for a number of reasons.
- Hex map support
- Easy to learn
- Easy to get a server running... usually
- I've been a player in it before, albeit briefly
- Solid macro language
- TokenTool lets me make tokens from character portraits
- I can make a dungeon map very quickly
- Good support sites like RPTools Tutorial
And of course it follows Rule #1, in that many of its features add to the fun of the experience (such as customizable visibility boundaries and lighting options). Some of these features - like per-player visibility - actually go beyond ordinary tabletop play, and are easy to manage as a GM.
My intention is to use MapTool similar to the battlemat at home - mostly to see a map and where things are on it. I'll also use it for player die rolling, although I will probably continue to use Dicenomicon on my iPad for the GM rolls.
The initiative system will also have to be ported into MapTool, which is the most complex task I face.
Anything other than Maps, Dice, Initiative, Tokens, and maybe a Gems generator is futured - I've learned the hard way to keep the first phase of a project minimal, to avoid the fearsome neverending-project monster.
I will post more on MapTool as time goes on, including some of the macros I create to support the Phoenix ruleset. Baby Bat will be helping me QA, so hopefully it all turns out fairly solid!