Now that the Fail round's wrapped up I figured I'd offer some feedback. I'd like to preface this by saying you've stumbled on a golden concept, there's a lot of potential with this. That being said, I have noticed a few issues with the execution that I'd like to address, in the hopes that we have a smoother experience for the Mario and Community rounds.
First of all, as a host in general, one of your primary responsibilities is communicating with your playerbase. Frankly that's been a bit lacking, there wasn't any advance communication what date or time the game was actually going to take place, only an extremely short notice of 30 minutes. (Personally, I would've taken time to read through the Fail Awards again if I had an idea of when the game was actually supposed to run, but it effectively came out of nowhere.) Every other game, whether that be Mafia, KG, Scribble, what-have-you, always does this, because you obviously want your players to know when they should be here. You've already seen how this could backfire - it took over 4 hours past the intended start time for things to actually get rolling because all of the players weren't around. Having gameplay times clearly communicated in advance ensures your players know when to show up, are able to let you know if they're unavailable, and if they simply don't show up, then the responsibility falls on them and you're able to move forward without them.
The questions are overall pretty well chosen, but I do have a couple pointers here.
- Make sure your questions are clearly worded! "In shameless business decisions what is Nintendo known for?" is a bit awkward and potentially invites more confusion than if you had simply asked "What won Most Shameless Business Decision?" or something along those lines. This includes making sure the terminology you're using is accurate - the Coin Shell didn't win any awards, but it did win a Bonus Star, which is a distinct concept.
- This is especially important when certain questions can be subjectively interpreted! I would not personally consider Sparky to be the first character in the Fail Awards - he was the first character posted in the thread itself, but not the first character to appear in the ceremony proper (the opening, presentations, and closing). As you can see, "Who was the first character to appear in the Fail Awards thread?" and "Who was the first character to appear in the Fail Awards ceremony?" have very different answers.
- More subjectively, I would personally suggest avoiding questions that are effectively pure guesswork, as they aren't really fun or satisfying to get right. I can tell you that even someone who had looked at the thread in great detail most likely isn't going to take note of or remember the exact number of single write-in entries on an award. That's the only question where I thought this was an issue, for what it's worth.
The pacing could also use some work, 10 minutes is a lot more than needed to answer a question especially if looking through the Awards threads isn't allowed, which leaves a lot of downtime. (The time limit for answering questions also seems to keep changing and I'm not sure why?) I'd say 5 minutes at a maximum, and even that feels like it's stretching it. If your playerbase is attentive, and they should be, maybe 2 minutes? Aside from a snappier experience, it'll also reduce the time commitment a lot - expecting players to be around for 2.5 hours to answer ~10 trivia questions is steep.
Hopefully this feedback helps, both with the rest of this run and for anyone who may want to host something like this in the future. Like I said, there's great potential in this concept and I think it could very well become a mainstay of Awards season.