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I'll be honest -the "reader freedom" idea holds no interest to me personally. I don't want to read on my phone, any more than I want to read on my tablet (unless it is a PDF/magazine in which case I will *only* read it on my tablet). Each device has a purpose and its strengths. If I want to read, I take my Kindle. If I am in doubt about an opportunity to read, I take my Kindle. If I know I definitely won't have an opportunity to read - I probably still take my Kindle. The phone gets left behind more than my Kindle! The tablets for me are big fragile toys - nice for a bit of casual web browsing, magazine reading or streaming TV/video, but not for serious ebook reading with the issues of screen glare, battery life, comfort, etc. So for me personally there is never a desire to be reading the same book on a different device.
Anyways, back on topic. If your concern is not having a PC on all the time, why not get a small device that you can run Content Server on so you do leave it turned on? It doesn't have to be expensive - I presume you could even use a Raspberry Pi for this purpose if you want something super cheap. It won't solve the transcoding problem (since content server is read-only, won't do conversions on the fly) but it would give an awful lot nicer UI and be far more accessible than Dropbox (which is blocked by many places as a security risk).
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