Any date works.
I think it should be limited to posters on the site. So we all can get together and chit chat.
I would imagine many more than 20 would like to go, myself included.
My suggestion is this:
Pick the dates first, so the Blazers can solidify the night. Start another thread with some dates listed. Give it a few days and the 3-5 most votes get handed over to the Blazers.
As soon as that is known, take a count of anyone more than 100 miles away that would like to go. I am assuming this wont be too many, 3-5? I would offer them the opportunity first, as I know it would suck to live far away and read about all these events and this sounds like a great one to go to.

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Then take a tally of all remaining who would like to go and can make the date. If its more than the 15-17 presumed spots left, then have a lotto. Anyone who wants to go, messages you a number between 1-100. The people who pick closest to your predetermined number then get those spots.
At any rate, I would love to go if there is an extra spot. If not, then let someone else have this one. I live close and can attend many events and I get some good club seats to games throughout the season.
Oh and Sly? You should be drinking and eating for free (if not included with the suite) for all that you do for us man.

. If I'm there ill take care of ya that's for sure!