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I have a Mac and the Sony 505. I have no problems with getting books onto my Sony. I don't use the Sony Store though. All my purchases are from fictionwise or book-on-board or diesel or Powell's. Free or cheap stuff can be found at Baen or in mobile read section on the sony reader books forum.
The only problem you are going to have with purchases is downloading format choices. This is often overwhelming the first few books you purchase. Ideally, you want to get DRM free epub books (they don't require any conversion and calibre simply transfers them to your reader). If that's not available, then DRM free txt or html is probably the next best format. You then import the txt or html into calibre, convert to epub and load the epub onto the reader. After this, the format issues get a bit more complex as you move into DRM territory. I personally strip all DRM from any purchases I make so that I can move the books from any device I am reading to another at any time to read how I want to read, not how the book companies tell me how to read. This requires a bit more knowledge on stripping DRM. I find it the easiest to remove microsoft reader's lit or mobipocket's DRM, but methods are available to remove pretty much most of the DRM types around these days. Just need to do a search (even on mobile read will give you links to other sites with the necessary info). After removing the DRM, then you import into calibre, convert it, and transfer to the reader. Once you are used to doing this "workflow" it usually takes less than a minute or so to get the books into epub and ready for your reader.
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