Like most other legal questions involving the on-line world and geography, these are not yet settled. Even if the legal guidelines found in this long list of related fields were fixed and the proper analogies were known, the sheer amount of information involved is a problem. Relying on related fields for information about sysop law creates uncertainty because nobody understands all of these fields in detail. No law-enforcement official. And no attorney that sysops can turn to for advice.
Every attorney has strengths and weaknesses.
A sysop seeking advice should discuss this issue with the attorney up front, together with the scope of the representation, timing, and costs. In summary, sysop law is very unsettled. Answers can be found, but proper answers generally come with several alternatives based on different underlying assumptions, and rely on adequate research.