I have some answers, pretty versed in this field. Don't take my answers as fact though, every Agency works a little different.
Couple of questions if anyone knows regarding Det. Holes.
What year did Det. Holes begin working as a detective? Don't know, usually would take min of 5 yrs to become detective while on force.
In what jurisdiction did he work in? Was it a jurisdiction now associated with JJD? Are you asking about city, county jurisdiction? A California officer Post Certified can work anywhere in state, will normally let local jurisdiction know they are investigating in their area. A police officer has all investigative jurisdiction once completing required courses, small departments may have one officer doing many things. One thing is for certain, a crime must have originated in his jurisdiction to investigate it. Wherever the crime occurred, the local jurisdiction will be lead investigators and control of case, sometimes the feds will have jurisdiction if federal crime i.e., bank robbery, kidnapping, crossing state-lines. Other situation is that small department turns over to county due to complexity of case or ask for assistance, they have better resources.
Was he assigned to just one case and so which one? The answer to this is most likely "no." Department could not afford putting one case to one man, even big departments.
Did he also work on modern crimes as he worked on what we now know as JJD related? Most likely, most detectives are assigned hundreds of cases at one time depending on size of area.
Was he always employed by a department or was he a freelance detective? Pretty sure he worked many cases at one time, never heard of freelance detective. You might be implying working on case on free-time, not being paid.