Use the 360° View in the Content Collection. 360° View can let you know if files in your personal My Content folder are actually being utilized in a course. Use this to review and possibly decide to delete any old material.
Organize your course using the organizational tools. Use the organization tools in your course (Content Areas, Folders, etc...) to keep the course neat and easy for students to find the resources they need.
Attach files as an Item. You can attach as many files as you'd like to a single "Item" either using the paperclip in the text box or the attachments option. Upload to the Content Collection and then link to the files!
See what students see with Student View. Utilize Student Preview to explore your course as a student would. Is everything laid out in a way that makes resources easy to find? Are your tests and assignments accessible and set up the way you intended?