Wisdom of buying high priced digital gear (given new advancements underway)


Wanted to ask for thoughts from others on the forum who have been playing with digital front ends longer than I... I only recently dove into streamed hi res music given the Covid shut-in...(although I am climbing the learning curve pretty fast)

I have been an avid trader/tester of good used hifi gear for many years now, a cost effective way of auditioning and understanding high end pieces in my own system, my own home.  Not for publication or posted reviews, just for my enjoyment and improving my own rig.  Buy smart on the front end, can usually get all or most of your money back when you sell, so it is a fairly low cost trial and ownership experience.

As I am fairly new to the world of stand-alone streamers and DACs, as well as combo units like a Hegel amp with onboard DAC, my question is whether it is wise to buy some of the more expensive high end streamers and DACs, say in the 3-4-5 grand (and up) range.

For instance, a Bluesound Node 2i is a capable digital bit-source (weak internal DAC noted) at only $500, so I question the benefit of buying a $2-3-4k unit from Innuos, Brooklyn, Auralic etc etc?  But if I do, just to try them, I am concerned there will be newer units out in the future, and these used units may take significant value hits.

Same thought for high end DACs... there are so many DACs out there, from high-value units like Chord, Schitt, RME for around a grand (or even less) -- what is the downside risk of climbing the curve of diminishing returns to get, say, for example, a Denafrips Terminator or PS Audio DS or Chord Dave for $4-5-6 grand used?  

I guess what I am really asking is what is the relative stability of the technology, product development, and the trickle down effect in the streamer and DAC markets, and does this materially affect the loss of value for the higher priced units more so than with old school analog gear.  This is something I feel I pretty well understand for speakers, preamps, turntables, the like...but not so much for the digital stuff, especially as streaming is really developing fast on the high end scene in recent years...

Thoughts welcome.  Thanks in advance.
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I agree with @lwin . I own an Audio Note Dac and preamp. The preamp has been upgraded and the dac will be next.

I’ve approached this issue two-fold:

1. I separate my streamer/transport/network server from my DAC to provide greater flexibility in future system changes.

2. I have chosen a DAC manufacturer who not only makes upgrades available but always has a generous trade-up policy. In my case Lampizator - who only depreciates the DAC by 1% monthly off the MSRP when applied towards a new upgraded unit. So even after 2 years I can still apply 76% of MSRP towards a new unit if I feel it presents a good value.
One's perspective is very much based on one's budget ... so I don't think there is any one "right" answer.  Given the rapid rate that the technology has advanced, especially with respect to DACs, that I view DAC years very much like dog years.  That is why I personally prefer to maintain the DAC as a more or less stand alone component.   I'm more comfortable with the idea of a DAC with an integrated streamer than I am of buying an integrated amp for it's integrated DAC.   My amp is 20 years old now.  I picked up my preamp in 2004.  I've had my speakers since 2011.  But a year ago I bought a new DAC and moved a DAC that I'd had for less than 5 years to a second system.  Nothing wrong with the old DAC.  But the new one simply was that much better for around the same money I'd paid the first time.  
I paid $1560 last month for a new Benchmark DAC3B. I was thinking this would be a good backup DAC  or a DAC for the second headphone system I am also building. Well it turned out that the DAC3B sounds extremely good to my ears and the thoughts of spending more on another DAC do not make that much sense to me anymore.

I think my Benchmark preamp, HPA4 is likely the reason this DAC sounds so good. The noise level on these 2 components are almost non-existent. I am getting a new preamp next week for the second system and I will test the DAC3B with that preamp to see if it also sounds the same. The second preamp is not as quiet.

My plan is to use neutral and quiet components on the preamp and DAC and add some sweetener with the amps and maybe speakers. I think some of the more expensive DACs have some flavor to them which people like (maybe the exception being the Mola Mola Tambaqui).

For a streamer, I use the Sonore microRendu. You can get them for $429.  I paid something like $700 for mine 5 years ago. It still works great.

https://www.smallgreencomputer.com/products/microrendu
Maybe analogous to smartphones. Yes the tech will increases rapidly but that’s a great thing!  Would you still wish to be using an iPhone 4?

Before someone quibbles with the analogy yes of course the rate of advancement is different across the industries but the general point is the same. With much advancement comes much improved sound. 
Whether to pay for it?  As always a personal decision