Worth pursuing analog sound from digital?

I hated digital when I owned bad dacs (for me they were all bad ,too digital, harsh, piercing highs even when they were not piercing they were like craking chalk on a board even subtly like that sometines   etc)…. I owned someday a NOS dac with a minimalistic design and that was game over for me... This incredible dac was too low cost for being mass convincing... (starting point systems dac)The sound was anything but not digital...Organic and natural...Viva digital life...

Wow the record side is over already ! I haven’t finished reading the album.  That’s analog for ya.

The most critical part of digital playback is ANALOG - the laser reading the data part. AND it’s the part that messes everything up. Ironic, ain’t it? And you can never recover. Boo boo! 😩

I agree that since 1995, compression is one of the three greatest causes of bad/poor quality recorded music. However, in the 1970s-1980s, pop/rock was often compressed on the finished product. I have plenty of examples where the Pink Island British pressings are fantastic and the U.S. pressings were crappy sounding. How about the Beatles U.S. versus British pressings. My British pressings sound really dynamic, tonally rich and listenable. My Capitol pressings often are compressed, bright, hashy and noisy. Not very fun to listen to.   I had at least 100 classical music cassettes from that period and they sounded dynamically compressed and generally awful sounding compared to the LPs (and not just U.S. but from Philips and DGG).  CDs, once I could play them better in the mid-2000s, obliterated the same recordings on cassette.  

There are two parts to getting analog sound from digital. It's not hard. Even I did it.

First is the source. The second is a DAC into the Amp (So many good Dac's out there now). I agree a DAC need not cost a much as a car new or used. As others have wisely said, wait until next week. These days DACs are falling out of trees.

Many folks crave analog sound. A good DAC can deliver that.

I get a lot of music from high res files from Qobuz. That matters. Depth is depth. 

I now use a Lumen T2 with a built-in DAC that goes to my tube set up. I also use an ungraded power supply with the Lumin. It doesn't sound at all "digital" nor would I put up with that. I'm a warm sound set up type.

A friend and I listened to John Coltrane's "Theme For Ernie" (SoulTrane Album) and "Blue rondo a la turk" (end drum roll is so system telling) first on his fine vinyl only system in his sanctified listening room and then on my set up (PLuna HP/KT120's..tweaked pre amp tubes…quality connects…yah dah yah dah yah dah) and Mr Vinyl only was astounded. As was the guy over last night who we finally had to say good night to again and again before he got the hint. He did sample King Sunny Adé, and that was nice to hear again.

To answer your question with out battling over vinyl verses digital:  In a nut shell, analog sound from digital is here (in the beginning it sure wasn't)....your set up...room..cabling...all will affect your system's sound. Duh. Simply great files washed in a great DAC is stunning as is a great pressing on a great (read $$$) vinyl set up. 

All this passion here is great. I read for a long time before daring to jump in. The overwhelming advice time and time again is if you like something then that's great. Duh again. Additionally gleaned is that so much is system/room dependent that results vary. 

I suspect at heart there are a lot of nameless, faceless tinkerers in this august forum. Everyone is proud of their babies. And they are all beautiful.