I agree, like in any designer/client situation (on or off this site) the goal is for the client to be 100% happy.
I think the simple solution would be to have Design Contest simply require an update of brief before an extension can be made. If the designer chooses to do that via response to a specific designer/designers then that also helps. Otherwise just a general addition to their brief. Having worked in many many one-on-one situations with clients outside of this site I realize it sometimes takes a bit for a person to really even know what they are looking for. But by the time the end of a contests original end date comes up, they certainly know what they don't want if they haven't chosen a winner. The very least they could do would be to add it to the brief, or something.
Truthfully that would be helpful to not only the designers, but to the CH as well.
My opinion is that on this site, there are hundreds to thousands of extremely talented and capable designers. If after a week or two of submissions, often in the hundreds, a CH is still not seeing what they are looking for, I think it is safe to say that there is something amiss with their brief or lack of communication to the designers. Which in the end both parties suffer because of.
These CH's are paying out only a few hundred dollars for thousands of dollars worth the work by designers, so I don't think it would be too much to just require a bit of feedback/further info if they are going to extend.
Then everyone wins!
**EDIT**
Another quick note is that there is a problem I see as well, not to be too specific, but if a prize amount drastically undershoots compensation for the amount of work required in a design, the CH simply can't expect to have as many responses... In that case, how long are they to be able to extend and extend. If the entries aren't there it's because as designers we know the worth of our work and it's unfair to expect endless entries where 99% of the designers are already working for free. To then have even the winning designer ultimately have worked for less than an hourly rate is a bit off as well...
Edited by kristijp, 28 March 2014 - 08:22 PM.