If I understand you correctly, you want to set it up so that for every package pair linux-image-<version> linux-headers-<version> attempting to install the former results in also installing the latter? And you want this to apply not just for a specific version number, but for every version number, including ones that haven't come out yet?
I was hoping I can add some rule based on regex in /etc/apt/preferences.d that will accomplish this. Well, if there isn't one then there is nothing much I can do.Just off the top of my head, I don't think there's any way to accomplish that. The only possible avenue I can think of for adding an effective