I wonder if you could use Fiverr for achieving your goal. I've been active there offering content writing services and I see lots of people offering a whole host of advertising opportunities.
For instance, for a Fiverr, you could write a company's name on your shirt or shorts (wear pants, more space
). Buy all white! You could probably reach your goal easily, the community seems to eat that sort of stuff up. Be sure to make a video describing what you'll do, they love video ads.
Just a thought.