Welcome to the slippery slope.
You’ll have a 252 and 300 in no time 
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I agree with the words of caution!
I can also see the appeal of streaming, adding that capability at home has opened up masses of new music. I added streaming progressively, for modest initial outlay. I bought a Chord Mojo and used my phone as the transport. Mk 1 Mojos going cheaply at the moment since the release of the MK2. I suspect a few hundred would get you a Mojo (other similarly priced options available!), you’d need a 3.5mm to DIN lead, and a streaming subscription, and off you go. If you don’t like streaming, sell the Mojo on. If you like streaming audition a few boxes and use the Mojo for headphone listening after its replacement arrives.
I can also see the sense in a CD transport in favour of the infrastructure required for ripping and storing and streaming locally.
But mostly, take your time - and enjoy it. Flipping heck, enough going on in the world that a few minutes listening to some great music feels like a total luxury at the moment.
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Atom to 252/300 in 12 months here. I’d never have jumped straight into where I am. Certainly not advocating my somewhat scatter gun upgades , but is has been an education and fun.
And it sounds now like the sound I had in my head.
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There is something to be said for enjoying the journey - rather than rushing headlong, to the end goal… 
But, each to their own… YMMV, etc.
I wonder what justification you have for saying that, in buying your system, you wouldn’t have jumped straight into where you are. Why ever not?
If you want to buy a car, do you start out by buying a Mini, then part exchange your way up to, say, a Jag with two or three cars in between over a period of a year or two?
You must have a wealthy and happy dealer!
We’re at a slower pace but 300DR and upgraded speakers are on the cards. On our new rack there is (purposefully) a space for the extra 300DR box although SWMBO doesn’t know it yet She did ask why we need 8 slots and justification was 6 naim + Sky Q.
Already discussed speaker options with dealer but there are new models on way soon which might pique interest so amp will come first.
Major stumbling block will be aesthetics as SWMBO paid for our current SF, likes the sound and look and isn’t sold on a change 
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First time I see so many people not pushing someone for upgrades. Maybe it’s the energetic crisis syndrome 
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If I were you I would avoid this forum and spend the time listening to your music instead - otherwise you will be convinced in no time that anything less than a system with 552 into a 500 is not worth owning!
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What can I say 
I’m a flawed individual.
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The olympica nova look very similar. You could probably get away with a sneaky swap.
Unfortunately I don’t think they come in piano gloss black 
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If going into the world of streaming the ND5XS2 will work well enough. If you upgrade your NAC to a 282 it will be more revealing of the source and you might want to upgrade the DAC of the ND5XS2.
I had an ND5XS and upgraded the DAC and in the end upgraded to an NDS with 555PS. My LP12 also ended up with upgrades so that my sources were equally good.
The point I am trying to make if you upgrade one thing you can end up upgrading another to balance things out. In my case I upgraded my amps first, then sources.
The key is to get a balanced system and enjoy your music.
The ND5XS2 with CD transport makes sense. Maybe leave it there. If you go for a 282 which is a great preamp you will end up wanting a better source and may end up with NDX2 plus 555PS.
With Naim there are endless upgrades, powers supplies and cables to bring better performance. Sometimes this can leave you obsessing about your system rather than enjoying the music.
Take your time and enjoy what you have.
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This thread is becoming ever more ‘preachy’. People here are adults and can surely spend their money as they see fit.
Instead of the Naim Forum, maybe we should call it the Nanny Forum.
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All getting a bit too much for me also
The ‘preachy’ responses are - perhaps - in response to the less-that-well-informed questions being asked…
Its the Modern Way it seems. Why read up on & try to understand something…? Just post questions on the Internet & get others to do the thinking for you. And if you don’t like their answers, tell them they are wrong.
YMMV…
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Good point! Where can we sent our invoices for consulting services to?
It’s all starting to sound a bit like “a Naim amp isn’t just for Christmas”.
I’d seriously question whether a CD transport is a sensible purchase. When I got my first streamer (272) I purchased a QNAP NAS and ripped all my CDs to it. At the time I had a CD5XS used as transport but, rather than trade it in, I decided to keep it for occasional use, as I anticipated playing the odd CD now and then. I still have it and I sometimes wonder why as I never use it. I guess it’s because of nostalgia (it was my first Naim purchase) that it still has houseroom. YMMV of course, but I certainly wouldn’t buy a CD player or transport alongside a streamer now.
Roger
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We should be more honest here. The forum is indeed full of interesting threads, but one of its appeal is to have the pleasure to spend the money of others. We should confess that.
I plaid guilty.
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