Funding is a bit rough for Americans, at the moment. I have gone through the process with the DAAD and Deutschlandstipendium twice (both rejections), and several political parties. First, your German has to be almost fluent. You will have an interview about your application, research project, goals for studying in Germany, and future plans. Second, and unfortunately, the funding targets for the federal government has shifted towards Asia and Africa, which makes the limited scholarships designated for North America even more competitive. Finally, you can only work a maximum of 20 hours a week during the semester as a student in Germany.
Despite the negatives, you have one massive plus. You are a native English speaker! Throughout my program, I have been teaching English and doing some English editing for fellow students. If you can carve out a niche, you will find plenty of work that can sustain you. Another bonus would be having some German skills (at least B1). If you have both language skills, then finding work will be easier, but still fairly difficult.
Sorry if I sound a bit pessimistic, but the past couple years have jaded me a bit about funding for foreigners in Germany.