I'd be willing to pay for ongoing development related to downloading the latest version for various amounts of time. I.e. xxx$ for a year to download the latest version and it keeps working (just like lms) if you stop. As I see it Squeeze really caters to 2 types of users, those who have large music collections and audiophiles who care about high end digital files. Hopefully more work could be done to improve that experience. Just my opinion but chasing after the services won't work.
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