Working With an Illustrator

I am working with an illustrator for my manuscript who doesn’t live in the same town as me. His job is to provide illustrations, photos, and charts that will clarify a point that I am attempting to make. It would be helpful for him to see the point that I am making in context as well as any additional notes that I want to share with him about the illustration. It would also be helpful (but my no means necessary) to compile for him a master list of illustrations, photos, and charts that the whole project will require. At some point my editor will want to see this master list as well. The document will also have other kinds of comments in it that I don’t mind the illustrator seeing, but it may be helpful if he can simply navigate just the illustration comments as he works. What is the best way for me to communicate these things to my illustrator. I may want to send him stuff chapter by chapter and then will send him the document as a whole. Fortunately, he is also a scrivener user, but like me, is also a newbie. Thanks.