Highest Possible Sound Quality from iTunes

[Confused]

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Or go down the J River route with the CAD. Assuming J Remote will let you do the stuff you need to do. Mind you you can always run a remote access screen…
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OR

-- and let me say right now that I know this is probably a stupid suggestion and may come across a bit flippant even though it isn't --

in Confused's case, maybe just forget track ratings ever existed, pick the thing that you like using the most, as well as liking the way it sounds, and then enjoy rediscovering your music all over again with a new system.  Half the stuff you rated as 5* you might not even like anymore, and you might have grown to love some old 1* and 2* classics of old that you've probably not heard for years    

Guillaume - That's the beauty of the CAD CAT, versatility!  It runs JRiver as default, but if you want, you could use it with JRiver & Roon, or anything else that works on a PC. It would also work fine in the future with something that does not even exist yet. (Say a Roon killer player comes out in 2017, or anything else) - Versatile!

Hifi_swlon - all suggestions are gratefully received on this thread, no matter how off the wall.  (although the last one gets only 1*)