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You should change the DLDB part. I've gone pretty much inactive and there are still leftover unapproved stuff left in there. I see no reason why PMs can't work, except that some problems apparently arose in the last contest in the area. Besides, most people would probably prefer not showing off their maps to the public until the contest finishes.
You could have a compromise. PM or DLDB method should be okay, because of all the problems with inactives, debacles from the last contest, etc., whatever the situation is. As long as it's marked [For the Map Making Contest], it should be a way to enter, even if it's though another site.
On another note, the openness for judging is quite the problem. As other people have stated before, there is conspiracy, rigging, revenge, and other situations that could cause a good map to fail horribly. I think one would be wiser to stick to a panel of judges, and if they want to compete, get some benchwarmer and replacement judges to judge for them. Probably a staff of 7 sounds okay enough. Not that any one is going to read my opinion.
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1)Does it have to be holiday themed? Or can it be anything?
No. Anything, as long as it falls into the rules from the first post.