I don't represent the ENnies officially in any way, but I can offer my interpretations from working with them as a publisher for 3 (going on 4) years. At one time they did accept e-mails, but that quickly got out of hand (e-mail can get lost, judges with CD have access to the products regardless where they are viewing the material, and a CD in the mail in something to look for and note if it got lost in the shuffle).
As far as I know, there is no flat fee for publishers who wish to place their product for consideration, but you are correct in that they have to eat the cost of shipping product and the physical product itself. Most of the judges up until now have been in the US and Canada, but shipping locations will vary based on the judge selection.
If you are considering entering, I would suggest taking the option to ship to 1 location and pay the minimal fee (last year was $10 or $15 if I'm remembering properly), because it may turn out to be less expensive than mailing 6 packages across the pond (the first pound is always the most expensive

) It also means that you contact 1 person to see that the package got there instead of 6.
*EDIT* Additionally, there wouldn't be much point if the end result is going to be a public vote. My products aren't well-known enough. If it were all based on the assessment of a panel of expert judges, I'd be much more tempted to risk it.
I understand what you mean-being a small publisher is a people's choice type of awards is not easy. This is less of the case in PDF (where PDF-only products with limited numbers of POD reign), but again, it doesn't negate the point you are making.
Think of it as a 2 tiered award. Judges (albeit publically-selected) read over all this material, discuss and pick what communally they consider creme of the crop. If something is not selected as a nominee, but it was close, they often give it an honorable mention so the public knows it was close. Then it becomes a public vote.
So with that in mind, Joe and I really look for the nomination, that nod of recoginition that we are making good product. We still tell all our fans to vote and make an honest attempt at taking home an award, but there have been years where we are nominated but do not make it up the podium, and that's ok. Heck, there have been years where our product was not nominated, but we showed up for the award to support our fellow publishers and the awards.
Just one publisher's perspective.
And if you have any specific questions about the awards and how they run, check the site. There will be a lot things that get solidified in the upcoming weeks. If that doesn't answer them, drop the coordinators an e-mail with your questions. They are very helpful.
-Suzi