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I think #2 could be managed by a good account registration without a fee. RPGNow doesn't require a fee.
The question becomes then, is can you get enough content that is worth paying for in order to cover the bandwidth costs and the storage costs? It's a good question. That's probably where someone like YC comes in. They provide the seed money to find out. I'd be eager to pay to watch some independent films if I knew that the creator got a good share of the profit. Of course, there could be a whole rating system, and you could find people with similar taste that made recommendations, etc.