Your situation is very far from unique. There are many service businesses like this -- plumbers, real estate agents, hair stylists, tanning salons, lawyers, carpet cleaners, restaurants -- that are ubiquitous and inherently local. That's why the decision is so easy for us. We treat them all alike -- list them in the smallest regional area that contains their home office(s).
And yes, we know perfectly well that some of these folk travel to their clients, or customers travel to see them. We don't judge how far people might travel. It's more a matter of how far people would have to travel to find one -- that is, do we have too many of them to categorize any other way?
This decision has nothing to do with where anyone's computer server is (although we have been abused for NOT taking that into consideration....) It's about where a physical presence is physically located. It's about the center of the service area (which is well-defined), not its extent (which is not).
It's not subject to debate. Any discussion of the guidelines' application to specific sites would occur in the internal editors' Regional forums.
However, we are sometimes willing to put service area in a description -- and that would not be an unreasonable aspect of a travelling DJ service to mention.