I posted some of this in the original thread, but I am posting some of it again.
Funding: Okay, funding can't come from the companies/people submitting products. Sorry, it just can't. Even if you make it "voluntary" people won't feel that it is voluntary and any large donor that wins is going to spark discussion of corruption. Even if such charges are completely false, the taint on an award is something that should be avoided at all costs. To have a truly respected award the even the APPEARANCE of impropriety must be avoided. If you want to ask for fan donations, fine. If you are going to be the GenCon awards, then by all means make Peter pay for all of it.
Shipping to Judges: (already discussed above, but here is what I posted before) I don’t know what others are going to say, but I am saying, um, no. Shipping costs can be very high, I admit that, and boxing individual sets of books, etc. takes time. It takes time from the publisher too. Most of the publishers submitting are going to be small, asking a small print publisher to ship 5-6 individual shipments instead of 1 per product is asking for a significant increase in the amount they need to spend to take part in the contest. Overseas and Canadian publishers might even choose to not to enter. If you want as many publishers as possible entered, make it as easy as possible for them to submit their products, don’t add additional steps.
The award itself: I am about to say things here that are sure to get me flamed. So be it. Some of the EnWorld members I saw at GenCon admitted to being surprised at just how huge the convention was, and how few people had even heard of EnWorld. I know people hate to hear it on these message boards, but in the overall rpg market, ENWorld is hardly a speck on the windshield. While a .pdf publisher with a following here might receive extra sales from a nomination or an award, print publishers hardly see a blip in sales. While most gamers use the internet, especially in this day and age, only a small percentage of those use it for gaming related questions, reviews, discussions, or even purchases. Avoid marginalizing the award by keeping it focused on DnD and related products, the further you expand the more you will be ignored, either because you are a DnD site voting on things you "don't know" or as an award that is simply overly broad.
Improving the Awards: the biggest improvement I see as being required is getting more publishers to take part, particularly WotC. Remember, big companies essentially have nothing to gain by winning a nomination or an award, but can certainly lose face if they miss out. Sure, nobody wants to compete with the “big dog” but if the “big dog” isn’t there what does the award really mean? Maximize the number of companies entered in whatever way you can. If the big guys don't participate, the awards mean very little. I think you should also work on timing, find out when the big parties are and make sure the awards don’t conflict with them. The White Wolf party was the same night and time as the Ennies award ceremony.
If you are going to be a general gaming award, you need to make significant changes to your structure, voting system, etc. You can’t have an award covering all gaming systems with judges and voting based on a DnD/d20 website. Okay, you can, but nobody is going to care. You also need to get all of the big players involved. If you have an award that is supposed to cover all gaming systems but WotC, WW, and Steve Jackson Games don’t even bother to enter, you can simply forget becoming enough of an award to have any broader recognition. Without market influence you are simply a vanity award used to garner recognition for people working in a largely unrecognized area. Up the costs for a publisher to enter, and that publisher is going to decide to recognize their writers and artists with special dinners or perks instead as these are cheaper, and are deductible business expenses (shipping you books isn’t). If you tell WW that they not only need to send you 6 copies of their World of Darkness book for judging, but that they also need to send each individually to one of the judges what are they going to say? (Hey, Steve is a great guy, he might say yes) From a business viewpoint you are asking him to jump through hoops to submit one of the very best selling WW books ever into your contest, a contest that has 0 recognition from WoD fans and won’t do anything to his sales. Hey, I love ENWorld, but if I were him, I’d just laugh and “file” your request.
I have seen several people post in the other thread that publishers shouldn’t be part of setting up the awards, or giving our opinions on how they are run. You do what you want to do, but if you start making it a “pain” to enter the contest, not many companies are going to enter, the fewer companies that enter, the less anyone is going to care. Make it easy to enter and do your best to get the big companies involved, without them, the awards are simply not going to achieve the recognition you desire.