Help for an Old School Audiophile

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.

Start with a Tidal subscription and your smartphone. There are a number of ways to get the files to your hifi, the easiest being wireless internet. If you have an iPhone, an old Airport Express works great, if android, buy a used Chromecast audio. Both well under $100 and can stream CD quality. You can always use a cord.
The older Airport Expresses, older Apple TVs, and Chromecast devices have digital out, which you can hook up to a better DAC. A Schiit "Modi" for $100 would be a fine place to start, but there are hundreds of options, and a google search will quickly have you tunneling down the rabbit hole. I say get the Modi and enjoy it while you are sorting all this out. Most likely, as the designer of the Modi says, it will end up being all you need.
Forums like this one will drive you to audio-nervosa in short order. For what it’s worth, an Airport Express and a Schiit Modi will get you better digital than most anything that was available 10 years ago; any reasonable person should be quite content with that. Move on from there.
As far as your collection of media, you may well find that 95% of it is available on Tidal (Idagio if you are a classical buff; I have both). I have a collection about the same size as yours, and I hardly ever touch it. If you have a lot of rare and esoteric recordings, you might digitize those, but from where I stand why digitize, store, and fret over something when I can just pop it up on Tidal.
Now if you want to go "better than CD" Hi-Res, MQA, DSD or have $tens of thousands to spend, don’t listen to me. If you are a vinyl record enthusiast, I’m guessing you already know how to make that work.
Most important, have fun and enjoy the music!

Thanks again for everyone's input here.  Its now 2 years later since I started this thread, I'm now 58 and still haven't done a thing towards digitizing my collection.  Instead, I've been playing around with some different setups, buying, selling, trading gear, enjoying the hunt of finding stuff and hating it the next day.  The summer always seems to be a buyer's market as lots of people put away the hobby over the warm summer months, wanting to be outside and active while the weather is nice as opposed to inside listening. 

The Spotify on my old Iphone actually sounds pretty darn good when it goes thru nice electronics (Muse Model 100 amp and Model 1 preamp & a Gemtune GS-01 EL34 SE int amp) and I find myself wanting to sell or trade my gear for other things as opposed to all the learning and time it will take to digitize my collection.

Nooooooooo! Keep your vinyl.

CD on a Nagra is musical and involving but switching to vinyl on a VPI TNT 1 with Benz Glider is that much more musical.