I have never liked the idea of consecutive events. Hosting an event is nothing like just running one challenge thread. Even though it's over in a month, that makes it all the harder. Along with hosting, you're working on emblem(s), the challenger list, the idea for the challenge before it's even up, your own playthrough, questions in the thread (have you guys ever noticed that there's always that ONE rule that is always misinterpreted? kind of funny tbh), etc. And then there's stuff to do irl as well, lol. Plus one every month, or even every other month would make them feel less special.
It's an ideal thought really, but it's just too much to manage, I'm afraid. I don't want events to be stale, and people need time to do their other challenges, games, homework, things irl, etc. Events take a toll on me, haha.
Hate sounding like the bad guy, but yeah, events every month just aren't going to happen. :(
As for the hardest challenge I've done, the Christian Challenge was pretty ruthless. No evolving, no Dark, Psychic, or Ghost moves OR Pokemon, no use of vitamins...the struggle was real. If you want a real challenge, definitely try that. It's pretty intense. If it weren't for Heracross, I don't know what I would have done.