I’ve done a lot of research on this community in my upgrading path to an (within budget) ultimate setup. But just to be sure (before buying); is a Chord Qutest fed by a Wiim Pro Plus really a day and night step up from a CD5si?
Nait 2 - CD5si / Wiim Pro Plus - NACA 5 - Neat Motive SX2
To my ears they sound totally different. To some the Qutest will be amazing, and to others it will lack a little something special that Naim bring to the party. As ever only you can decide.
We have compared the CD5si directly with an Audiolab CD transport feeding the Qutest DAC. No contest - the Audiolab/Qutest was head and shoulders above the CD5si. In another league entirely.
I have no idea about the streamer you mention though. It appears to be low cost, but my guess is that yes with the Qutest DAC it will easily better the CD5si. The DAC seems to be more important in setting absolute quality. And of course you can upgrade to a better streamer later.
Having said all that the Qutest does have a very different voicing to the CD5si. With the Nait 2 there will be a certain synergy with the Naim player. So even though the absolute quality may not be up to the Qutest it may end up sounding more enjoyable.
You know the answer - you really need to suck it and see.
There isn’t a Chord dealer in my neighbourhood, so I have to trust reviews and experiences. Maybe a used Ndac is a safer choice… or just stick with the cd5si.
If you want to play CDs then the CD5SI is the very thing. 
I’ve read the Nait 2 needs the best source you can afford. I really like the cd5si, but if a qutest or ndac is significant better…
You will have to compare to really decide but for straightforward CD playing the CD5Si does the job for me with my Supernait 3.
I don’t know where you live, but where I am, with no dealers of any sort near, I auditioned my original Hugo, and later did a full audition of two other Chord DAC, by “mail order” from a dealer called Nintronics, London way I believe, I had to pay full price, to be refunded upon return, and all worked well. I had to pay return carriage, which seemed fair - and far less than travel costs were I to take a trip to audition.
I had a Chord Mojo on loan and it sounds great, but very different than my CD5si. More clinical. I guess the Qutest sound is similar. I’ll stick to spinning discs in the cd5si.
Or, perhaps more to the point, it is the only thing if you want a current Naim player.
Before Naim stopped making their more expensive CD players I suspect that the most appropriate match for the Supernait 3 would have been the CDX2 But as it’s no longer available…
That’s why I bought the CD5SI warranty and repair ability for a little while anyway.
I like the no frills and I don’t have to have a collection of remotes.
I have not heard a Mojo but I certainly wouldn’t describe the Qutest as sounding in any way clinical. It is neutral sounding, without the added warmth that the CD5si brings, but it is incredibly involving and communicative.
However I think you’re probably right in that it isn’t the best match for a Nait 2. Bare in mind that the Nait hails very much from the days of LP, when it’s natural environment would have been with an LP12 as a source. The LP12 back then was certainly warm sounding and the CD5si, whilst I’m not suggesting it sounds like an LP12, has a similar warmth and generous bass.
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