I wouldn’t reject @Igel ’s suggestion out of hand. Personally I found UPNP via the app nicer to use than USB when I had a 1st generation streamer, but there are plenty of people who like the USB approach. It’s probably the simplest way to start using your lovely NDS as it will just mean copying files to the stick.
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I think all the advice here is good, but may be confusing. I would suggest you do it in three stages over a long period.
Stage 1 - simplest option
Copy all your music to a USB drive, and plug into the NDS. This will simply and quickly get you listening to your music.
Stage 2 - Run uPnP from your PC
This will be downloading a uPnP server like Asset onto your PC (gets mentioned a lot here), and pointing it to your ripped files. It will categorise all the albums/artists etc, then you point your NDS to the uPnP software. Fairly easy, and you may be able to get a “try for free” licence until you know what you want
Stage 3 - Ultimate option is to get a NAS drive
This involves a purchase, and adding another box onto your network that contains disk drives. You can use this as network storage also, but the main thing is to install a UpnP server onto it, then copy all your ripped files across, and point your NDS to it instead of your PC. That way your PC doesn’t have to be on, but your NAS drive will always be powered up.
IMHO, I think stage 3 does add a bit of complexity, depending on how IT literate you are, but going through the stages gives you plenty of time to build up your knowledge. Also there are loads of people here to help you through each stage.
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100% agree the GadgetMan Plan.
I would add a shortcut and go from stage 1 to 3
But if I can also say that when I made the CD to Streaming move 8 years ago, I went from CDX2 direct to ripping to & playing from NAS, nothing in between, easy, simple & fast learning fun.
That’s what I would do if I was doing it again.
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With a NDS, 552, 500 system , I’d be tempted to look at an Innuos, I had a Synology NAS with a linear power supply, I only needed to hear the beginning of one song to realise the Innuos was on another level . They’re also easy to set up, easy to import music to and it did a better rip than dbpoweramp.
Full disclaimer, I only have a 272 and 250 and have never heard a 500 system, but the Innuos brought a lot to my humble system, I could only imagine what it would do for a NDS, 552, 500 system.
With such a good system and a NDS you should consider a real music server if the budget allow it. The good ones improve the sound quality (beyond a computer server like a NAS) and they come ready to use.
The obvious choice is the Naim Uniti Core. I have owned and used it and it is really fine.
The other ones I know, and currently use, are the Melco. They have several models. The Melcos have the advantage of not needing a network switch - you just connect the NDS directly the Melco and the Melco to the network.
But start by talking to your Naim dealer about a Naim Core.
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I may have missed this in your post but I hope u are aware you need and xps or 555ps to power your nds? I stream on an nds, it makes a superb digital hub, once you bond with it don’t be surprised if u spend 98% of your time streaming from tidal!!
I’d assumed that as the NDS is replacing a CDS3 there would be an XPS or 555PS freed up from that.
I suspect I will start with this approach. When I have acquired the knowledge and gain confidence, I will the try the other suggestions.
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This is the most logical response to my query so far. And you are right about the advice given by all the contributors…really appreciate it, guys.
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Im in no hurry, so will probably follow GadgetMan’s advice. 
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I do have an ps555.
That would probably be my long term plan. But how does these 2 different systems compared to a NAS setup? Is the NAIM better than the Melco, or visa versa?
Yes. I have both…XPS2 and 555PS. I couldn’t decide which one to sell because they both sounded different on the CDS3…depending on the genre of music I was listening to. I suspect the 555ps will be more suitable on the NDS…
When I had a Nac552,I was powering the NDS with 555PS DR and now I have done some downgrading and have an XPS to NDS but it still sounds very good using USB sticks.
If you hold your ripped music on a PC (including on an external hard drive) as I do, then you will connect the PC and NDS to a network such as your ISP router. Wired connections are best if possible. Some newbies do not realise that you do not connect the devices directly.
The server software (on your PC) and I use AssetUPnP provides the UPnP stream that your Naim app can receive and control. Using AssetUPnP server software is simple and provides greater flexibility and searching (i.e. by Artist, Album etc.) in accessing your music than using a USB.
Start off by keeping it simple - too much confusion puts people off streaming. I have been streaming for 7 years.
All the things you mentioned have been capable by way of a PC. Streaming is connecting to a source like Amazon, Tidal, Spotify’s and paying for accessibility.
Amazon sells inexpensive streamers. Additionally you might want to look in to BluNode.
How do you find USB sticks sound wise to this option ?
You would need to have your Pc on whilst accessing the music. Using a USB stick or external USB drive eliminates that. Or has been said a NASdrive.
I’ve got. 1Tb Usb Solid state drive which just plugs in the back of my naim
Which is also on 24 hours to access your music!
I have a dedicated PC with 2TB HDD that runs 24/7/365. Not been switched off for years.
Not tried it for years and that was not on an NDS.
They are the same files so should be no difference.
You should be aware of Naim 1st gen issues no one has mentioned - wi-fi, flac/wav, Qobuz etc.
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