The last question in the challenge is at least a reasonably good one. It’s pretty easy to answer too — the best DM I’ve had is my brother Tom.
Sure I’m biased but having been a gaming club in college and played some convention games and so on I’d guess I’ve played with at least 20 or 30 different people as DMs (or GMs in non-D&D systems). Good DMs are few and far between and I could only think of two or three other DMs I’ve thought did a really good job, maybe a handful of competent ones, and the rest were kind of crappy. Tom stands out for running memorable games — the only campaigns I ever really mourned when they ran out of steam.
He’s always been pretty good at improvising and making up interesting NPCs on the spot. This has served him well as he avoids railroading and per-conceived plots most of the time. As far as I can remember he’s never run an “out of the box” campaign and rarely used modules. Having looked at a lot of the published modules now I think he was right.
What really makes Tom the best DM in my eyes though is the simple fact that he has been able to recruit new players very easily. Once they play in one of his games they seem to be hooked. Perhaps the down side to this is that when we were younger, we moved around some and in every gaming group we joined, Tom displaced the old DM. This may have caused some hard feelings, although it was never an intentional power play. What would happen was Tom would offer to run a session and nobody wanted to go back to the old DM. Somehow he’d keep the balance between being adversarial and not challenging enough just right. We always felt that surviving an adventure was an accomplishment and while we sometimes teased him about being a “killer DM” or bending the rules (one player in particular dubbed him the “freewheeling DM”), he was actually scrupulously fair. He showed no favoritism, ever — not to me, not to his girlfriend, not to anyone. He also never “had it in” for any player, and if anything was too charitable to kick unpopular players out.
His only weakness as a DM, in my opinion, is that he rarely keeps a campaign going for very long. In fact he won’t call his games “campaigns.” He prefers running low to mid-level adventures and enjoys episodic rather than continuous story lines, so I don’t think he ever really sets out to run a long-term game. I could probably count the long-term campaigns he’s run on one hand, really, and I don’t think any were in D&D. Still, since I have been DMing for a few years in a current group run an ongoing campaign, I hold out hope that at some point he’ll want to DM again and might even try a long-term game for a change.