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I can't comment on ADE under Wine, but ADE under Crossover works a charm. I have bought books and put them on my reader without issue. I have an Astak Pocket Pro, and the closest thing I had to a problem with ADE under Crossover was I needed to mount the Pocket Pro THEN run ADE, otherwise ADE didn't detect the reader.
So in point form;
- ADE installed under Crossover.
- My computer and reader were authorised without question
- I was prompted last week to update ADE (ADE would close if I didn't update it). Worked fine (needed to download setup.exe and re-run that in my ADE bottle).
- Have bought books etc and all have worked without issue.
I have not been able to (like the OP) get the Sony bookstore software to install under Crossover or run under a virtual machine.
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