Well, one thing is for sure, this topic has created a lot of message traffic. Given that he's a veteran of the cons and having his own booth, whatever he decides to do will be measured and evaluated.
Whenever I think of a raffle, I always think of something I can't afford (or do not want to). It's almost like gifts....the best ones to give someone are something that they wouldn't buy for themself. Most of the classic covers are simply too expensive for this purpose so what about reprints? There is one classic book that every collector wants.....an AF 15.
How about a copy of the True Believers AF 15 reprint put out 3-4 months ago in CGC 9.8? I think the price is cheap enough that you could also throw in another title, like the ASM 1 or the IH 181. Pick 2....both in CGC 9.8 and I bet that will come in under $100.
I think any collector or fan would love it. It's a great prize as these reprints tend to up over time since that is as close as many collectors will come to the real books. I would also go down to a $10 purchase per ticket.....