I think there is a bit of daydreaming up in this thread, but lets go with it...
One thing to seriously consider is that the VAST majority of chiptune is released for free or as donation-ware, even the absolute best artists, and I don't see that changing any time soon. So competing in that area is going to be pretty much impossible. Like as with any indie musician at this point.
Also outside of the chiptune community, the genre is completely unknown. Think of what CDK said: in the whole world, there are like 5 or 6 regular chiptune shows, and those are SATURATED with booking requests (if boston8bit is any indication). So, ahem, [marketing speak: go!] what you need is another growth market, and that is going to take some sweat-equity on your part: Build your own local scene.
As you said, New Orleans has a rich musical culture and would be a prime location. So, start your own concert series, book well-respected "national" artists and develop local talent. Expose New Orleans audiences to chiptune. You will bring in new fans to chiptune, and bring the scene to you. Everybody is happy.
Its hard, its expensive, its time consuming, but it is rewarding and from my perspective, the only way.