Markus1299
For a couple years I used a MacMini for my digital music source. Converting Flac through the use of other programs and trying to work my way through an endless stream of work around programs to make my optimized mini listenable. It was just okay, I then had an opportunity to experience PC audio. No work arounds, whatever you download is there right now whether it's Flac or whatever.
I nearly gave up on Mac too. The AIFF files my Mac ripped did not sound as good as FLAC but FLAC required the work around you mention.
Sure, you can drag FLAC into Channel D and tag them so iTunes accepts them but what a PITA. Then two programs must shake hands and work together and iTunes sounds bad compared to JRiver.
Now that JRiver for Mac is out. Friends in high end audio that are Beta Testers for JRiver told me absolutely no difference in sound with Mac or PC, provided both have proper chipset, memory and cables.
JRiver 19 for Mac is wonderful and JRemote works just as you are currently experiencing with Windows.
Since you have PC working there is no gain to move back to Mac but for those reading this thread you can have great sound either way.
Go with what you already own, or purchase which ever operating system you are comfortable with.