Just to follow up. This is the process I have to use to load library books using Overdrive/ADE and Sony Reader library with my PRS-300.
Notes:
Haven't been able to use Calibre with library books.
This worked for me on Mac or PC.
This is only with pdf version library books.
1. Checkout book from library website
2. When asked, I select Open Using ADE
3. Connect PRS-300
4. Close ADE
5. Open Sony Reader Library
6. File>Import Files
7. Libraries>Documents>My Digital Editions*
8. Select the pdfs of the library books then Open
9. Drag the book from the library to the PRS-300
*on Mac, use My Digital Editions Library location
This seems to work consistently for me.
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