At the senior center where I belong, many members now have e-readers. And many of them had problems understanding how to get books from the library. The senior center did several programs on e-readers, did multiple sessions showing how to get e-books from the library, B&N, Amazon, etc. They also have members that have answered many questions from other members.
The local library has people on staff that are familiar with various e-readers. They also got students from the local colleges to come in several hours per week to answer questions and help get patrons up to speed on borrowing books and so on.
I think this has worked well for the last year and most everyone that wants to read ebooks is comfortable enough to get things from the library if they wish.