This is a few thoughts from writing Small Basic forum monthly challenges for 3 years.
Initially they started as weekly challenges, here is the first, which was in response to a discussion topic posted by Kirkkaf. However, the weekly setup was just too fast a turn-over. It was difficult to create them every week, and only one week did not provide enough time to let contributors work through longer challenges, so it was changed to a monthly event. There have been a couple 'guest' writers of the challenges over the years (most notably rubbikWizard) and usually there are some great suggestions for the following month from contributors which I always incorporate. These are especially welcome as they breathe new life and perspective into it.
Nonki wrote a wiki article listing the previous challenges, and Jibba Jabba collated some statistics.
The nature of Small Basic is that most new programmers use Small Basic for between a few months and a year, then move onto greater things or otherwise fade from the forum. So the challenges have to cover basics and I also try to add some quite tricky ones along the way. The main idea is that contributions will show different ways to do things. Some will be 'better' than others, but the variety will help new programmers by seeing how others tackle things. Basically the community can help each other with a continually evolving set of programmers at different stages of experience at any point in time.Here are some of my observations:
I look at and run them all, even if I make no reply, and enjoy seeing progress as people 'get-it'.
From my point of view it is hard to gauge the level to post questions at - the more replies to a certain type of question tends to lead to me creating more of this type, but this doesn't mean these are the most helpful. Another issue is continually trying to create new and original ideas, especially for the smaller simpler questions.
So, here's some questions: