I am going into my senior year of college in upstate New York and looking to land a job with a startup in the City. Should I start contacting them early on e.g. October or is it better to wait until I'm closer to graduation?
Worst case scenario, they ignore your application and you re-apply close to graduation.
Best case scenario, they offer you some freelancing or part-time work and you graduate with some real experience and, potentially, a guaranteed full-time job.
I'd recommend making a list or just have a few startups you like. Find their founders and cold email them personally. Perhaps try to meet them and then build a relationship and then get to the ask i.e job.
Another good way to meet startups is to attend tech events. Go onto meetup.com and search for tech meetups in whatever area you're interested in. Consider favouring topics like Clojure programming seminars over things like "networking and margaritas for SEO rockstars" or whatever. The crowd will be smaller and more personal (and, in my contrived example, probably more technical!) and you will have a better chance of getting recognised as a regular participant in a small community. You get bonus points if you also volunteer to present an interesting project or something.
Worst case scenario, they ignore your application and you re-apply close to graduation.
Best case scenario, they offer you some freelancing or part-time work and you graduate with some real experience and, potentially, a guaranteed full-time job.