Help for an Old School Audiophile

First off, I want to thank everyone for all of their comments and advice. 

After seeing the powered DynAudio speakers played thru the salesman's phone, I was more curious than anything else and also knew that I knew very little about this kind of stuff.  My post was therefore more of a fact finding mission as the future is inevitable and I wanted to see what others were doing with their systems.  Truth be told, it doesn't sound as fun as watching the record spin or my cassette rewind.  So whatever I do, I'm going to take it in a slow progression.  The other thought in writing the post was that if, one day, I scrap it all for convenience and minimalism, or moved abroad but wanted to have lots of music, how would I go about doing that and the answers provided give me a very good starting point.

I do not have a desktop system and do enjoy my home system and listening to FM radio.  As a Lyft & Uber driver, I listen a lot more to Pandora in the car than I do at home.  When I want to listen to Pandora at home, I just run an RCA to mini plug into my phone and listen thru my system; however, at home, I usually find myself either listening to FM radio or one of my other sources (LP, cassette, or CD). 

Sound quality over convenience is a lot more important to me and at this time, I don't mind taking the time to change albums, cds, etc; however, I guess its all what you are used to.  For those used to the convenience of a music server and Tidal or Roon, you probably wouldn't want to take the time to change records, etc when you can instantly push a button and have music play instantaneously.

I'll re-read the entire thread as it's a lot for me to understand and digest and I thank you for your ideas, thoughts, and opinions.

Update - my nephew recently set up Spotify Premium on my phone so I got rid of the free Pandora.  This is a huge upgrade from the Pandora and I'm enjoying making playlists for my car. 

My daughter has told me that it's time to just get rid of the 2 tower cases that hold those 10,000+ songs on Itunes because I can now get all of that music on Spotify.  

Baby steps, I get it, but that's how it's gonna go.  I also just got a new cartridge for my Thorens TT too.

You haven’t made it clear why you want to digitize.  I am 70.  I have about 500 CDs of classical, and about the same in rock, blues, folk.  

I thought about digitizing and opened another thread on it.  But in the end, with the quality of my speakers where a cheap CD or an MP3 is clearly audible, I decided to stay with the CD’s.  Another member talked about 2 friends who digitized all their CDs and now wishes they still had them because of the sterile sound that the digital music from the computer had.  Perhaps they should have used a $2000 DAC(digital to analog converter).  We surmised that jitter is a pretty serious problem when you have too many digitals in the pipeline.  

Well, CD's are digital, sampled at 44.1 Khz.
But listening straight from a PC sound card has limitations in sound quality.
It is really pretty simple to begin, but you can get as complex as you need.
First, download a media software program like J River (others may have different program recommendations). 
You can burn all of your CD's directly through J River into a file folder of your choice.
After that all that music is available on your PC or Hard drive when you open J River.
The music is shown as a file complete with the cover art.
Just click on the file and you can play the complete CD or any song on it.
Now regarding sound quality, you will want to obtain a good DAC (digital / analogue converter). The DAC is what will give you the quality of sound from the PC. There are some very good DAC's that sound close to analogue (nothing will replace pure analogue audio). I happen to like the R2R ladder Dacs that have become popular and no, you won't have to spend 2000.00 unless you choose to do so. After that the RCA outputs on the DAC can run into a pre amp, integrated, or headphone amp depending on your system. Pretty straight forward and you're off to the races. Never have to open another flimsy CD case again. 

About a year ago I decided I wanted to move into streaming my own music.  I had a collection of around 400 CDs and 1000 LPs.  I have four very standard and I suppose “old-fashioned” two channel Stereo systems,  the main one an almost high end living room system centered around Quad ESL-63 Electrostatic Speakers and a French made tube integrated amplifier, CD player, tape player and turntable.  

Not necessarily relevant, but I also have three other full featured stereo systems in my house and, like you, good quality of audio is important.  For example, I’ve never used iTunes because it’s all as far as I know in degraded MP3 sound.  I had hoped to get them all playing my streamed music.

My nephew helped me get started and recommended I purchase a Naim Uniti Core which has a reputation for very good audio.  It also has the capability to rip all my CDs, contains a pocket for storing an internal hard drive which holds all the ripped music in its new digitized format, including the all important metadata.  Lastly, the Naim device also acts as a streamer when activated by a corresponding Naim app for my iPad.  Sounded pretty simple and straightforward.

 When my nephew told me I needed a DAC to connect the Naim streamer to my audio system to convert the digital stream from the Naim to the analog format expected by my stereo system I realized I had a concept problem and that’s when I started to realize I was in a complicated new environment.  Never having the need of a DAC before,  I didn’t really understand why I needed a DAC.  It seems dead simple now but my point is that when you dip your toes into the digital world that you are asking about, you will find it chock full of potentially bewildering options and a bazillion acronyms,  It took me a long time to get reasonably conversant in this new environment.  In hindsight I think a picture would have been worth a thousand words.  In other words,  I think what would have most helped me would be visiting a dealer or a friend who has something set up reasonably close to what I  wanted to achieve.  I tried to get educated by reading and it seemed to take me  forever. But you need to do both or you won’t likely understand what a dealer will be telling you!

Just deciding on a starting point is potentially difficult because there are a lot of different equipment makers out there for both streamers and DACs.  DACs can be particularly complicated because there are many competing ideas on how to achieve the all important digital to analog conversion. Some can decode only PCM, others add MQA and a few can do pure DSD. And you’ll want something that can decode the highest resolution music stream.   See, already those acronyms crop up and initially I didn’t have a clue what they meant.   And there’s a lot more to it than that.  So buying a DAC can be complicated.  And they can get very pricey.

There are also all sorts of options for ripping and storing your own music.  The Naim made it really simple for me, though I’ve since discovered it has limitations.  I don’t think I’d choose it again.    Someone mentioned  Bluesound.  It has a lot more features than my Naim Uniti Core making it a good starting point because it greatly simplifies getting started.  Like the Naim, it has a ripper and internal storage and unlike the Naim, I believe it acts as both a streamer and a DAC. It is at the very cheap end of the equipment possibilities, so if your budget is more flexible, keep looking.  But my point is, keeping it simple in the beginning is not a bad idea.  Otherwise you get into more complicated software choices and storage issues,  like investing in a NAS for example..  (There’s yet another potentially mysterious acronym).

I hope this helps get you started and good luck.