As a developer, I think the closest parallel or most common way people do this is to be "the web guy" for a few businesses: part-time, ongoing small development

As a developer, I think the closest parallel or most common way people do this is to be "the web guy" for a few businesses: part-time, ongoing small development and maintenance. I've worked with many people like that through the course of my work. It seems like a chill life, but I don't know that I've seen anyone scale it to more than what the average freelancer gets.