There is really only one rule to hosting a TD: This is YOUR game. Let your personality shine through and have fun with it. At the same time, however, running a TD is time-consuming, so you want the highest return on your investment.
Over the past few years, I've become aware of one psychological quirk of human nature: People are always unconsciously looking for reasons to not do things. Make it easy for players to enter. Whether your rules are too tricky or your topics are too obscure, the more twists and turns you throw in, the fewer entries you’ll get.
And no matter what, even if it's your tenth time at the helm, it never hurts to ask someone for feedback on your game: both the rules and the questions. I am always happy to help out, and I know several others here are, as well.
Keep the questions general: think Trivial Pursuit categories. Exceptions can be J! wheelhouse topics, such as U.S. presidents, British monarchs, world capitals, and Shakespeare. When my focus is general knowledge, I aim for at least one general question in each Trivial Pursuit area.
It's much better to make the questions overly easy than to go for obscure or niche information. Ask yourself: can everyone playing this game give at least 2 or 3 correct responses? If not, I'd suggest ditching it, or refining it to make it more accessible. There have been several times when I started my entry for a TD, got hung up on one question, put it off for later, and forgot to submit.
10-12 questions is ideal. More questions means more fun, but too many questions will scare people away. I like for each question to have between 9 and 15 possible responses: large enough to give players options but small enough to force them to think through their decisions.
Do as much as you can on the front-end – particularly writing tight, accessible prompts to cut down on clarifications later. JBoard has a lot of members who are good at sniffing out technicalities. For example, when I asked for the "number of men on the field at the start of a professional soccer game", I knew I was asking about the number of players, but what if they were women? Do the refs count? (Trivia writers call this "pegging the question.")
Mix up the presentation! Images break things up and might even attract players on the fence. I like to think at least one person entered TD 271 just because they saw my map of the U.S. and said, "Hey, I know most of those interstates!"
If it's your first time running a TD, consider the bare minimum in terms of additional rules. DROP (zero points) is easy to implement and is universally understood.
If you're ready to throw in a wrench, keep the quirks simple. More strategy is fun, but there are quickly diminishing returns with increased complexity. You'll have to spend time explaining how things work, and potential players might be too confused to enter.
Personally, I never offer a SHEEP option (automatically take the highest score). The only reason to have a SHEEP is if your questions are too obscure. Fix those instead.
Penalties for incorrect answers should be tied to some variable: either the sheep score for that question or some proportion of the number of players. Fixed penalties can be advantageous to later entrants, as I found out when I offered 11 points.
- Obscure one-off responses with a low bar for qualification. For example, "Name a character who has appeared on Family Guy" is a bad question, because some random appearance by an otherwise-unknown character makes him eligible. If you're willing to go through every minute of footage to get the complete list, sure, go for it; otherwise, expect some pushback after the reveal.
- City populations. The distinction between "city limits" and "metropolitan area" is confusing. For example, New Delhi proper has a population of 250,000 but over 20,000,000 live in the metro area. Do not expect your players to know the difference.
- Billboard charts / AFI rankings / box-office take. I generally don't know if an album sold 20 million copies or 20,000, or whether some quote was picked by some subjective committee, or how much Titanic made (whether adjusted for inflation or not). If you do use a question like this, add some extra information – perhaps the director/star of the movie or a line from a song in the album – that could help players zero in on the correct answers.
- World capitals. When I ask about them, I always put lots of disclaimers about which alternate/planned/de jure cities I won't accept.
- Rankings with an arbitrary cutoff. If you're going to ask for the top X of something, make sure there's a big gap between the last possible answer and the first incorrect answer; perhaps even give the identity of the first incorrect answer and why it failed to qualify. Take particular care to peg your definition properly here.
- Jeopardy! history. Yes, this is JBoard, but questions on the show tend to draw a lot of ire.
Feel free to add your own thoughts and experience below!