100 page outline? 30 page outline? Really? If your outline is more than 10 pages and the exam is NOT open book, it is worthless. You need an outline taht you can memorize. You really can't effectively memorize more than 10 pages. I would recommend grabbing some treatises really good supplements. Look at the table of contents of those treatises and compare that to your syllabus. Where the areas overlap, draft an outline around the main points. Add the big ideas to your outline. I use this initial outline (which generally takes a weekend to complete, within the first week of the course) as a roadmap. I use it to familiarize myself with important concepts so I know what is important so I can spot those concepts in cases very quickly. Then, on a weekly basis, I update my outline for what I learn in the courses. Generally, I have to revise the outline once a month because it's very difficult to synthesize rules without seeing the big picture. It takes about a month to complete a module, sometimes more or less. When a module is complete (i.e. character evidene say for evidence or Perfection for secured transactions), I synthezise the rules for that section and revise the outline around those sythesized rules. My weekly reviews generally just incorporate the material for that week and class notes (which are sparse, I don't believe in taking copious notes in class because so little of what is said in class is relevant to an exam; the more you write, the more you have to eventually wade through). This gives me two important advantages: 1. I review and memorize my outline throughout the semester, so by the time dead week rolls around, I know my outline like my right hand knows my male private part; 2. I try to stay at least a week ahead of my reading, so, by the time the last week of class rolls around, I'm not preparing for class, but instead doing practice exams. An extra week of practice exams is incredibly helpful.
Generally, my outlines consist of sythesized rules, one to two sentence case summaries, exceptions to and expansions of rules, policy objectives, and relevant facts and hypos that illustrate rules. Again, let me reiterate, my outlines are generally no more than 10 pages, UNLESS the exam is open book, in which case I annotate the outline and create a table of contents for quick use. I then take the 10 page outline and condense that down to a one-page attack outline during the two days before an exam. Basically, that outline consists of words or phrases to spark my memory to my larger outline or a strategy for how to analyze a question on a particular issue. That has worked very well.