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For myself, I have never used the Sony software, because, when it first came out (I had one of the earlier Sony reader models to start with) it was so buggy, and everyone was complaining about the issues it caused with their reader and computer. I just started using Calibre right from the get go. The Sony ereaders were great, but the interface software not so. Sony doesn't seem to be really responsive to user needs/issues, whereas Kovid and his team really do fix any issues that come up, sometimes in as little as a couple of hours of an issue being reported! (Yay Calibre!)
I wanted to have as few issues as possible, and have support when I had a problem. I did some research before I bought my reader and came to this solution. I've now had 2 Sony readers and various older PDA's and have used Calibre for my electronic library management software. I'm more than happy with the level of stability and support. Calibre has yet to cause any issues on either my desktop or reader.
My current reader which is a PRS-T1 will probably be my last Sony reader, since as of the PRS-T2, Sony has decided to remove the audio component from their e-reader hardware. Having text to speech on my ereader is a is a requirement for me, for a lot of various reasons, so even though I like the Sony hardware, I'll probably be going somewhere else for my next e-reader.
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