If you've never seen the 1999 American Movie documentary, you really need to. It's an extraordinary doc about 2 guys in Wisconsin (Milwaukee?) who set out to make a low-budget horror despite all odds.
What's so fascinating about this is how hard this guy works yet seems to get nowhere. He's a smart and knowledgable guy but his drinking and shortsightedness (like hiring his friends instead of experienced crew members) get in his way constantly, as he tries to make the ultimate American Movie.