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My household has a Mac and Windows PC as well as 350, 950 & T1 readers in use. For non-DRM you shouldn't have any issues in theory. And for DRM, as long as your ereaders and computers are registered to the same Adobe account user id, then it shouldn't matter which computer they are downloaded from and which they are transferred from. At least I have not had any problems. My Mac is getting old now, and I'm still using OSX 10.5.8.
It used to be painful, and I kept my book library in a virtual Windows desktop on my Mac. However, the Sony ereaders have played nice together for 2 years or so now. One thing to note is that ADE for Mac doesn't recognize the Sony ereaders has a connected USB device like the PC version does. So you need to transfer via an alternative method such as drag-and-drop, Sony Reader software or calibre.
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