I agree though if you've worked in the casino industry as long as I have there's precious few other ways to reason about what's going on in the minds of people who don't understand gambler's fallacy.
This is actually not strictly applicable: what SMBC is talking about is a game that is some portion gamble but for which there is a house edge or strategy that you can exploit for gain. A lotto drawing is purely random (read: no skill) so someone with sufficient understanding of the math is no better off than someone who writes in random numbers. The same is true for slot machines.
He knows full well it is very unlikely he'll ever win, but he enjoys the excitement/fantasizing that it provides him throughout the week.