Ok, different questions.
There is no generally accepted or IRS recommended way to document this stuff. Just keep all the paperwork: from the entities that give the scholarships, billing statements and so forth from the school, 529 statements, etc. I made spreadsheets that listed all the education expenses, both 529 qualified and non-qualified, whether directly billed by the school (tuition, fees, room and board, etc.) or not (books, required supplies, off-campus housing, etc.), and then showed where the dollars that paid each expense came from and when (loan, out-of-pocket from student or parent, scholarship, need-based grant, 529 distribution, etc.). This helped me strategize the most tax efficient way to fund the college experience, and it also made a great record to help me explain and defend how and why I did things the way I did, in case that ever becomes necessary way after I will have dumped that data from my brain. If you do it all above board and carefully document what you do, you should be in good shape.
