Can't stack send a t-shirt or prize to the person that submits the worst contractor/DIY disaster of the month or maybe have a running list for the year? I would certainly visit site and meta more if the top 5 for the month were rolled up to me. I have this month's first nominee - Why is my ceramic tile popping out of the floor?
I agree with keshlam in this case, anecdotes/funny stuff aren't usually the best fit for the main site. Maybe good for chat, though?
That said, just to put it out there, we certainly have no problem with supporting a community event/contest with an occasional shirt if you agree on one! Other sites do this occasionally. Code Review had an extensive best-of "awards show" at the end of the year, and Travel (just to name one example) does monthly challenges (I linked to an activity challenge but topic challenges are also common).