hello Nathan....you sound very similar to me when I was in high school....I wanted to pursue being a DP after buying my first American Cinematographer magazine....the path to become a Cinematographer/DP are very different, there is NO one path.
My thoughts are to shoot everything you can get and save everything you shoot, (except for porno's but will leave that up to you)....
From what I've seen, take any job that gets you in the door and where you can prove yourself to be talented and good to work with. I know of no crew job in Hollywood that is fulltime with benefits, like the normal job we all know about. If you can afford freelancing, then do that, but it takes a LONG time to develop relationships for the employees (Producer and other crew) to hire you....Being an AC is a great way to learn the camera, taking care of equipment, loading magazines or digital cards, etc....Being a Grip to Gaffer is also a great way to learn as well, since you get to know the electric side, lamps, which lights to use, etc....Another big help is to find an internship with a crew or DP....some offer pay, some don't, but you'll make connections and get your foot in the door..
I went to film school in Montana, but then worked in creative services/video production and learned how to Write/Produce, DP/Edit....a great way to learn, although you might be doing small car ads to furniture stores, but you get to work....
Video production companies are a great area too, which is where I work. You can get work with digital gear, dolly tracks, steadicams to lighting, shoot commercials to long form productions.....In these areas, you dont' have to worry about being in a union or paying dues, but if you are, make sure you make the right connections to con't to work....