I am moving away from Mac after 25 years of nothing but Macs, wondering how I do this with Roon and maintain all of my Roon data such as Covers, Playlists, etc?
I would stick with the Macs… but for Roon the Core seems to be more stable and in a better place on Windows IMHO … but it’s one of the only Windows system in my house, the rest all being Macs and very happily so.
Smart man! Welcome to the dark side! 
Before you do this can you tell us why? That way we might be able to help more.
Why I am leaving Mac? Well, without trying to launch World War 3, I have had enough of the platform, the Apple Ecosystem is a broken shadow of it’s former self and one that I have been working myself out of for some time. I think the company has stopped innovating and are no longer the only company making cool product.
On top of that I rather like Windows 10 having dipped my toe in the water several months ago by offloading my MacBook Pro and replacing it with a Microsoft Surface Book. I love the thing as it also replaced my totally useless iPad Pro which would have to be the most over rated and poorly named product to ever come out of Apple.
Like all of Apple’s IOS devices they are hampered by the lack of a file system, user expandability and are over priced. Finally these days, Apple are no more reliable than anything else on the market, so it is time to go fully Windows 10 in my world.
One final thing, the HP Z840 Workstation I intend to replace my iMac 27" Retina comes standard with a 3 Year onsite warranty, something that costs hundreds of dollars for with Apple.
Follow the guide Ratbert points to. I made the move a bit over a year ago to win 10 pro and my sound has never been better. I don’t trust apple and reports of some folks collections at full resolution turning into low resolution files was enough to make me jump, that and the reasons you mention. Moving my collection away from iTunes was the trickiest and I can’t remember all I did but I google searched until I found someone who did and followed their lead, it worked like a charm. My music is now 100% apple free, whoo hoo. Now I must admit I am typing this on my macbook air laptop which I do like, but my music will forever be mac free.
BTW- my music HDD are now all formatted in EXfat so, if needed, they can move between machines easily.
I have no axes to grind. What you are talking about has very little to do with the music system. It is mostly emotional and that is perfectly fine. So what are you going to use in your music systems? The Roon Core needs something simple and stable. Unless you are running multiple endpoints… The Roon endpoint is critical for the sound. If you are going to run windows there then you need to get the extra services shut down, etc… I know that a lot of folks are running Windows Server in their Audio systems so that managing services is simpler.
As far as moving between Mac and Windows that his mostly trivial. The files system issues are still there. But with an EXFAT or FAT32 external drive moving data is simple. The command key vs the control key,… I am sure that will not bother you.
On Windows be selective with your anti-malware solutions as those can take a lot of compute power.
Either OS can manage a Roon system well. Of course there are dedicated computers that will do it simpler sometimes. Some of them are running Linux and hiding that from you as much as possible.
I would like to see folks like Melco get their hardware working with Roon. The little silent machines from Small Green Computers are also interesting.
So keeping in the Roon space let us know how we can help!
Bob, emotion is not involved really, it is a decision based on Apple no longer providing what I need in a computer.
I am getting a HP Z840 Workstation with 8 Core Xeon CPU, plus everything else that platform offers, that NO Apple computer can provide me.
Keep in mind this is not a box dedicated to music playback, it is also my main work machine (I build web sites for a living) and I do multitrack audio editing as well as photo and video editing. To be honest Roon playback will be the easiest task this machine will do.
The nice thing with the Z840 is that I can put 4 internal 3.5" drives inside it, I can add a second CPU for even more grunt should I need it, and it is designed to run 24/7, unlike my iMac. Don’t get me wrong, I love the iMac it has been a good machine, but I have simply out grown it.
I would not worry about horsepower for that machine. Just watch out for processes that can disrupt the audio chain and have fun… There are a lot of tweaks you can try.
Well, the transition is complete, all went to plan thankfully. Happily listening to music through the new HP and eagerly awaiting the arrival of Roon 1.3!