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I get the feeling google may reward the pages if they are left looking like directories, but other engines may not crawl the pages at all.
1. Leave nothing at end of url, or put .html?
2. Do you think "-" would have better than "_"? I know anything is better than "index.asp?page="
I would go with www.site.com/content.html
The distance in PR from / to /this/other/page.html, is only as far as it takes the spider to find the link. If you link to it right from the main page, then it'll be weighted more(generally) than if you only link to it from a page in /this/other/index.html.