We are having this discussion locally due to the archiving of this year's Geocachers To Do List challenge cache in the north Texas area. I've read both sides of the argument and I have some comments.
So, the date rule (yea or nay) is going to be unfair to either newbies, who don't have a bunch of caches under their belts to choose from, or veteran cachers, who may have to travel a long distance to get new caches to meet the requirements of a date challenge. I'm sorry, but the decision to coddle the veterans rather than help out the newbies is pretty selfish. The current rule is like holding a golfing competition, but telling people that they can post their score from any previous round on that course, regardless of year. Pretty pointless competition, if you ask me.
And honestly, are there really areas that are SO SATURATED that no one is ever putting out new caches? Maybe some of those veterans need to be putting out a few more for each other, or encouraging local newer players to do so, rather than complaining that they have to travel too far.