Saying that the expected value of this strategy is undefined seems like underselling it.  The expected value is positive infinity since the cumulative reward is increasing strictly faster than the cumulative probability of getting nothing.  

This is a really interesting effort and I'm excited to see where it goes. However, as Zach wrote, this seems like a fairly long shot effort. It's a crowded primary field and the other candidates have money and experience in Oregon state politics. I'd be very interested in reading a more detailed writeup on the state of the race, the strengths and weaknesses of the other candidates, and Flynn's plan for a path to victory. I'm not currently convinced that donating is a worthwhile use of money, but a good enough plan might change my mind. 

I like this post, and your conclusion really resonates with me. One more resource that I think is helpful to point people to is Ozy Brennan's Career Advice for the Everyday Effective Altruist.