With me being AWOL for a while the fate of the online B/X game is a bit up in the air. What does the future hold? I don't know.
I have a few observations from the skype game.
1. I was either too polite in inviting/accepting people into the game or I needed to structure it differently.
Now, I want to make sure this is not misconstrued! I really enjoyed gaming with everyone that played and I am glad to have met everyone that participated but I think the game would be better with either a fixed group (making scheduling more difficult) or a setup similar to the Northern Marches campaign.
The Northern Marches campaign was an open campaign which accommodated the busy schedule of adults. It was structured so that whoever was in attendance could participate. This was partially accomplished through having everyone return to the one site of civilization in the setting or face Jeff Rient's Triple Secret Random Dungeon Fate Chart of Very Probable Doom. By having everyone return to the starting point, it allowed for a full roster of characters for the next session. One thing I found about the skype game is that the pace was slower than a face-to-face game so not as much was accomplished each session. This would make the Northern Marches structure a little more problematic.
2. The DM/Player interaction required to pull off a sandbox-style game is more difficult using an online medium.
A sandbox requires players with the ability to provide goals and this is amplified using something like skype. I find that in a face-to-face game a lot of this information is exchanged either when the group is just BS-ing or talking about the session just completed. This BS-ing is just not as natural with 4 or 5 people on skype. There are other ways of generating this communication such as a group email or blog for the campaign but they just don't work as well as when you can sitdown with the person.
3. I haven't gotten past the lack of visible feedback during play.
I mentioned this a while ago but it still bothers me.
I would definitely run more games using skype but I would likely do a few things differently and place more constraints on it.
Maybe by running a specific adventure module.