Regarding the paper-less part of the question, I think you need to be realistic about how much you can do by yourself. Unless you can get institutional buy-in or from support staff, you really have to triage how you do it. I can’t tell you how many hours I have spent by my trusty scansnap. Things have gotten a lot easier for me since most of the courts I appear before are on efiling. I don’t use naming conventions though. I use DEVONthink and have described my workflow here