I think what we need to talk about implementation. How does/should one purchase a raffle ticket or bid on an auction? If the auction page is a place to preview an item before it goes on the block, it should probably include dates of closing. There's a lot of auction software out there, some of it free. What's in the works in that area? Juro, you hinted that you and MattB were working on something...?
Anyway, I think membership should be membership and raffle tickets a separate entity, especially given the individual complexities of each raffle. There are some items that will require a minimum amount of tickets to cover costs. Membership raffles would be cutting into defraying that cost.
Membership, IMHO, should be there to cover the basics (server fees, photo and scanning costs, software purchases, etc.). Raffles and auctions are gravy and would garner funds for activities (claves, out reach programs, thank you gifts for clave captains, etc.). I feel it would be a mistake to join the two drives.
Also, why even call it membership if what you're really doing is selling a block of raffles. If we really want to add value to membership and have it mean something, I think development of an FFF pin or tee-shirt or something is essential. All groups need a means of identifying themselves. Raffle ticks just don't cut it. Give me something physical I can wear with pride at Big Girl Bar. At the very least, this model speaks to the idea of self perpetuating membership. The item becomes a conversation piece that gets people talking which draws in like-minded individuals, and in turn, furthers our cause. It has much more group value than individual chances at winning stuff.
Just my $.02 (ok, maybe this is more like $.03