I can't imagine a tougher route to take into the world of feature filmmaking than comedies. There's always a market for low-budget horror or sci-fi movies. There are plenty of people who love pretentious, minimalist dramas filled with shots of people brooding under harsh lighting. There are even groups of people who eat up terrible, no-budget action movies. There really aren't that many people who are clamoring for unfunny comedies, though.
It should go without saying, but the success of a comedy relies entirely on the strength of its humor. Sure, the other fundamentals of filmmaking are important, but if a comedy just flat out isn't funny, it's pretty much dead on arrival. That's why I admire any aspiring filmmaker who opts to make their inroads to the industry via comedy. Really, there aren't that many of those inroads to take these days. You can either do the Kevin Smith thing and make a grungy but witty and heartfelt story about the bitterness of becoming an adult. Or you can do the Woody Allen thing and make a stylized, self-deprecating but witty and heartfelt story about the bitterness of trying to find love as an adult.
Obviously those aren't the only two kinds of comedies in the world, but they are emblematic of the two most common paths indie filmmakers have tried to take over the years (though the feature-length sitcom is proving more viable thanks to the likes of Broken Lizard, Derrick Comedy and Jody Hill). With Stuck Like Chuck, twenty year-old filmmaker Jerry Cavallaro has confidently taken the Kevin Smith route, but unlike most filmmakers his age who attempt to emulate the Smith brand without ever acknowledging that they're doing so, Cavallaro openly embraces who he owes his style to and the result is a movie that is, and I say this endearingly, charming as f--k.