Legality and feasibility of digitizing old text books and course notes for private use
How did you handle it?
  


With an unstapler, a xerox/scanner with paper feed (and a few after-hours spent listening to my mp3 player and hoping the xerox machine wouldn't clog).


  
  Is it even legal to scan full text books for private use? 
  


This depends on your jurisdiction, but generally speaking it's probably considered fair use. Also, "no plaintiff - no judge". (Lest anyone asks: No, I'm not advocating anything illegal here.)


  
  Is it even feasible to scan dozens of books and folders full of notes and print-outs?
  


Books will give you a hard time, because they don't fit into the automatic feed. Notes and print-outs do. Have you considered paying someone for doing the manual copying for you (the neighbor's kid, a poor student etc.)? After you have the files, however, only part of the work is done. OCR'ing the files and saving them under intelligible file-names is still something that can be delegated. Digging up the references and ordering the files in some reference management software is the harder part that requires more or your own work or at least oversight.