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Here's what I do:
• Take the syllabus for each class, list topic headings with assignments in OneNote, Word, or whatever; and list the minimum reading, briefing (typically - casenotes, but I read the cases), etc. with estimated completion times…
• Then add the supplemental reading to the corresponding casebook readings - often, I'll read the supplements before the case book. Outlining the supplements seems like a waste, but whatever works for the individual is what works.

I prefer Understanding XXX, Gilberts, CALI, and E&E's (although, I thought the criminal law version sucked. Dressler's Understanding was awesome). I frontload since I have kids that are unpredictable, and I need the last few weeks for exam prep. I took a summer class using this method, and it worked good.

To expand a bit:
Once I have a list of all assignments and estimated competition time, I create a list of due dates. I use OneNote (see below) and each flag represents a task. The tasks created in OneNote are created in outlook simultaneously. The links within OneNote are to assignment pages, outline, and or PDFs. Then, after the task are created in OneNote, I schedule those tasks with Outlook into a calendar. For me, breaking it up is more manageable.

OneNote Task Page:
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Outlook Week schedule
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