2) Using startup-esque techniques like Recommended Articles and Verified users won't work, as it will kill the simplicity of HN (note that Reddit has tried similar systems not too much success). Content is the most important factor to determining upvotes.
3) Yes, there are a few articles by YC alumni over the years which receive suspicious amounts of upvotes, and I'm disappointed by that. (case in point, see the cofounder of ReelSurfer's submission history: https://news.ycombinator.com/submitted?id=njoglekar)
Flagging works for stories that are completely unsuitable for HN, but not product announcements that are somewhat relevant but not popular enough to reach the front page on their own.