I had a mid range Audio Note analogue setup to about 18 years ago. I bought it all used. I sold it to move to digital, and then the problems began! The digital journey, many have been on that one.
My SETs were Audio Note Conqueror Silver. Speakers were Kef 107s (disaster with the SETs), then Audio Note AN-E (borrowed), Avante Garde home demo (can't remember the model but was new out in 2009) then Zingali Overture 2s, then Zingali Client Name Evo's. I found the SETs were very organic and easy to listen too, but with decent tubes fast and detailed enough. The thing in the end I am a bit of a bass head, play loud and like the drama of music. SET was possibly a bit too intimate for my taste. My Plinius sounds tube like (yes that sounds wacked I know) but also has the drive and bass foundation and iron grip SS can give. It is also a warm sounding amp. I also got fed up with power tube costs and hassles. That and my lifestyle didn't fit having tube power amps I can't leave on. t don't get on well with colder sounding electronics, whether tube or SS, just my thing I guess. I do like detail and feeling the music is alive, but not in exaggerated way. My journey through DS DACs didn't go well.
Does that answer the question? Might sound rambling, but my audio journey was all over the shop I found. Buying used is quite good IMO, and you can always sell on at not so much of a loss. Buying new may be more problematic if you shift gear on an ongoing basis. Right now (finally) I feel grounded, very happy and the system sounds right to me. It is not so much a DAC here is better than that one there. I is also the synergy of how they interact together with the rest of your system (and your room). I have heard many top flight DACs that sound just awful with another top flight amplifier or speaker. It is not a sure thing, just like relationships Ha Ha. What I am trying to say is, some gear is just made for each other, and finding that is the fun in this hobby IMO.
Thinking a decent headphone setup may fit my lifestyle, in 2010 I bought a Stax SRM-717 amplifier and 007 HPs (Mk2s). I loved using them late at night when speakers would be a problem. I got hooked quite quickly on the fast and transparent electrostatic sound. It had something new about it that I found addictive. Later I had a DIY KGSShv built, then another one for a second system, then a KGSShv Carbon and bought the 009s. The sound from that is incredible, does something I have not heard in 200K speakers. So I run both the 009s and the Zingalis from the same source and a passive with output select. Works well. Funny, I stupidly thought headphones would be simpler right? No room acoustics to worry about. Wrong. The way the amplifier drives the HP seems even more critical. And they need a good source or they will remind you of it on a regular basis.
Apologies, I need to put this in systems or another thread probably. Will do that.
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