We (GF and I) also recently "won" on one of these scratchies offered by Classic Escapes Holiday Club. We attended the presentation, being the open minded people we are, and there's no question that the arrangement looks appealing. Your family and friends can use your membership, over 5000 places worldwide and the "extras" option which extends to stuff outside the 5000 places they have interest in. We paid the deposit ($700) knowing that we had a 7 day cooling off period - which I saw basically as a week to think about it, look into it, read reviews and forums etc. I have struggled to find much positive feedback, there's the occasional positive reply but those replies quite possibly are written by people within the company. It seems that the only people with positive stuff to say are the people selling the product. As for the original prize, we've been given the voucher but I'm not sure we'll end up taking it - as we still have to pay for everything else - travel to and from, meals, entertainment etc.
Short of getting in touch with a few members who are not employees of the company and hearing about some positive experiences we will exercise our right to a refund of the deposit and may or may not use the voucher.
My advice - If you can get together a group of people to share in the cost of the membership and all those people can afford to gamble their share on possibly getting a few good holiday arrangements over the 15 year period then it's probably worth the risk, because over 15 years you can probably work the system to get you a good deal on at least a few occassions.
Whatever you do - don't cough up $7K purely on the sales-peoples word that you are buying 15 years of awesome holidays that you can pick and choose - there just doesn't seem to be anyone that can verify this claim.