HELP! Importing Files to Music Server - Totally Confused

You should be able to connect a USB cable from the hard drive to your Music Server and complete your music transfer.   Check your equipment for the types of connections supported.  I suggest you do not use  Wi-Fi for this transfer process.  I also recommend you rip your files using an uncompressed format for the highest possible sound quality.  

Assuming you plan on streaming music (Tidal, etc) from the Internet to your Music Server, I strongly recommend a wired connection (hard wired).  Unfortunately, Wi-Fi will not result in the same sound quality.  I also did not have an Internet cable connection in my living room and used an Ethernet over power connection.  This means you use your power line to connect to the Internet.  This solution worked but I finally decided to hire someone to run the Ethernet cable under my house. This is the best solution for maximum sound quality when streaming. 

I own an Aurender Music Server and recommend their products.  See:
http://www.aurender.com/

I know you prefer the physical media (CD’s) but Tidal Streaming is amazing.  The music is uncompressed for CD like quality.  Album selection is very good.  You can always find something you like.  Tidal provides various genre playlists or you build your own.  Tidal has over 10,000 MQA coded albums for improved sound quality. You decide.  

I use an Apple iPad to control my Aurender Server and their Conductor App is very easy to use.  The App connects to my Aurender using Wi-Fi.   Other similar server products use the same technology. 

There are many posts on Audiogon on music servers and other useful information.  

@hgeifman ... thanks for the informative explanation. I'm really not interested in streaming, and running ethernet to the second floor of the house may be problematic. I'm getting into this "ripping" thing because I'm concerned that new, high quality CD playback equipment may not be around at some point, and my current high end player (MF Nu-Vista) is getting on in years. So, I simply want to try to keep one step ahead of being obsolete. I am somewhat of an old school Luddite, so this transition is painful and confusing. 

rlb61,  Okay.  I understand you are not interested in streaming and running an Ethernet connection to the 2nd floor is impossible.  Please note that using an Ethernet over power connection works fine for your application.  This technology sends the Ethernet signal using your electrical power lines using a small box connected at each end (source end and the router end).  

For example, see the NETGEAR PowerLINE 1000 Mbps, 1 Gigabit Port with Pass-Through, Extra Outlet (PLP1000-100PAS) below:

https://www.amazon.com/NETGEAR-PowerLINE-Gigabit-Pass-Through-PLP1000-100PAS/dp/B01M2WSIVD/ref=sr_1_4/136-3229033-8457622?ie=UTF8&qid=1523305110&sr=8-4&keywords=ethernet+over+power

Once you finish ripping your existing CD's to your hard drive, what are you going to play them on?  I am not familiar with this the Sony Hap-Z1ES you mentioned above.   I believe (please confirm) that you can copy your ripped CD's to the Sony and play them.  My guess is the Sony will run without an Internet connection but I do  not know.  

I recommend you rip your files using an uncompressed format such as the Audio Interchange File Format (AIFF).  It is an audio file format standard used for storing sound data for personal computers and other electronic audio devices.   The Free lossless Audio Codec (FLAC) is another audio coding for lossless compression of digital audio.

Music servers usually have a built-in hard drive for music storage, but most also have the capability to connect external hard drives.  As such, you could copy your files to the internal hard drive or merely attach the hard drive as an external drive to the music server.  My only concern is what file format you are using.  Not every music server supports every file format.  FLAC is very popular, but it's not universal.

Once I have ripped the CDs,I think I’ll get a cheap laptop with at least a 2T internal hard drive and get a USB DAC Stick. I’ll use a USB to RCA Y splitter to connect the laptop to my preamp’s Aux output, and will use JRiver or some other library management software. Since I’m not interested in streaming at this point, that should do it. What do you all think of my solution?

Not optimal,but it will work and as time and budget allow you may want something else.

Kenny.