I suppose my own nostalgia is what makes me so fond of the 2015 - 2016 era of Trivia, but the mods at that time had an extraordinary skill for bringing people together, and so a close-knit community was quickly built, where all those inside jokes of Sandshew, poisoned ice cream, hugging Slugma etc originated! Most of those regulars no longer visit the forums now, but they really helped establish Trivia's friendly, chill, community spirit that it has today. ^^ With members like you and the others keeping it alive, it practically runs itself! Because of that I definitely want to create something memorable for everyone before I (eventually!) retire.
As for organising events, there may be changes this year that I'm not yet aware of, but overall it works like this: members pitch an idea in the specified thread once it becomes available, either as a suggestion, or offering to host it themselves. They can also co-host it with someone if they wish. If they host, they get the Event Organiser role, and they'll usually have a few weeks to set everything up before the GT starts, with help from the GT Management. Then it's up to the host to keep the event running during the GT. You might have seen Who's That Pokémon and Spot the Difference hosted last year, though it's easy to miss, since the threads go into a dedicated GT section and not in Trivia, or anywhere else. Also, events don't need to be extensive or long! Even single-day events can be quite popular. I'm not sure if you've seen Aldo's article, but this is a great example of a GT event that represented Trivia:
https://daily.pokecommunity.com/2022/05/30/26-puzzles-to-test-your-detective-skills/
And I know what you mean, I feel the same way about Discord overall. Love the community it has established, lots of friendly members like Aslan who are very welcoming! But I also suffer social anxiety, quite bad actually, especially in new situations/groups of people, so I mostly use Discord just to keep in touch with a few old contacts. ^^ I also find it quite difficult to join in when there isn't a conversation I can be part of, since most of it is small talk and banter!
Thank you for the friend request, a pleasure to accept it!