With the assistance of Azzleflux, I made a not very original completely original, two-part challenge for writing an article. You can choose to do either by itself or do both, but the actual challenge itself is to do the two.
Both of these require some sort of die-bot or die-rolling program. Nala is capable of rolling, but you should probably do it in a PM if you plan on doing it at all, so as not to spam #site19.
1.) Go to the Visual Archives, assign a number to each archive (avoid the photobucket, as apparently you can't save the pictures)
2.) Roll twice.
3.) Go into each selection you rolled, assign a number to each picture, and roll again. One roll for each archive.
4.) Make an article using both pictures, no matter how unrelated or poor the picture.
EDIT: You can make minor edits to the pictures, to make them look better, match more (if, for example, one is greyscale), or if you want it to fit slightly more with the tags, but you can't blatantly add new content to the pictures.
1.) Go to the Tag Guide, click Attribute Tags tab.
2.) Roll three times (Mack says there are 173 attribution tags, so that might help you guys)
3.) Write an article that fits the three tags you rolled.
EDIT: If you have no idea how to make a tag apply to an article (any article, not just yours), don't understand it, or otherwise will end up poorly pseudosciencing a tag, you can reroll. Cheaters will know when they're cheating.
And that's the jest of it. The idea is that both, together, will provide a sufficient challenge for the author. I hope somebody tries it and enjoys the difficulty the two will hopefully bring. I'll try it out myself, at some point.