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  Not for publication or posted reviews, just for my enjoyment and improving my own rig.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.
17a97d8a 159a 4596 a0ff 0ccf132fd762Ag insider logo xs@2xjjss49
New advancements are always underway. Denying a purchase because something new/better will be coming out can induce paralysis (deer in headlights). The same thing occurs with photographers: they delay purchasing new cameras out of concern that a better model will come out after they bought the latest camera. But they miss the enjoyment and quality pictures they could be taking NOW. 
As noted it is a good idea to pick a company that offers solid software upgrades. For example: Linn came out with new versions of thier Space Optimization technology which is a major option and cost nothing for owners of Linn DSM boxes...

your point is well taken but the intent of my original post is to define a price point where purchasing modern digital gear makes sense (for normal people who value money and have competing priorities for spending of it) to get very good quality and minimizing the risk of 'wasting' money as things move on

i have come to the conclusion that about $1000 for a streamer (used) and $1500-1800 (used) max are the cut off points for me... i have tried several highly regarded streamers and dacs more expensive than these levels now, and i have formed my opinion of where the sweet spots are in their value curves - just my opinion, using my system, my ears, my sense of the value of money


don’t know about modi - it is schiit’s bottom dac... i tried a bifrost mb it was ok but somewhat sibilant, sold it, currently have a gumby in house, it is nicer for sure. warmer, clearer, less sibilant all at the same time than the bifrost as i remember it

if you want a really inexpensive dac to beat the pants off the internal node 2i dac i suggest a chord mojo... some ergonomic differences to be navigated but the sound is absolutely superb for how inexpensive that cute lil thing is

Thanks for the feedback, the chord mojo is the other dac I am considering.  The reason I was interested in the Schitt Modi Multibit is because it is considered a R2R dac and many think the R2Rs have a more analog or at least musical presentation.  Also, truth be told, its the least expensive R2R being sold.
Post removed 
The threshold for all this is up to the indidual. The “that’s just silly money” point for one person might be the bare minimum for another. 
I see a ton of “all DACs sound the same” and “don’t spend money on a DAC as it will be obsolete in a month” posts on audio forums. Its not like DACs stop working just because some new box comes out.I have a friend who has a 20-year-old Proceed processor/DAC and it still performs and sounds wonderful. It might not do MQA but the level of decades long service is commendable.

Buying this stuff is like everything else: do your research, audition (if possible) and spend your own hard earned money wisely. 
I think the important thing is paying attention to the used market: regardless of price range you want a box that has solid resale potential if you decide to upgrade or go in a different direction. Some tech and brands will go out of flavor which impacts resale potential. It happens. I am also a paddler. Long sturdy kayaks with rudders were once all the rage but today folks want shorter, lighter boats with a skeg. When to buy and when to sell is all part of this game...