Hi Gino,
I just took a look at your profile and noticed that you have a few higher impedance headphones, I would suggest a hybrid tube amp for those over the Jot only because you can tune the sound to your liking. The thing with neutural/realism/natural is its hard to say since what is neutral/natural to you may not be to me and I find that its something not worth bothering with as long as it sounds good to me, or as you say "the right recordings". I don't strive for the best or consider things like "HD800 is upgrade to HD600 "since to me there is no best sound signature, just different flavors, as in wine, woman and song.
My idea of what is sounds comes from being a musician from middle school until I graduated from college, I used to play a trumpet, guitar (acoustic/electric) and ukulele (Hawaiian instrument-like a small 4 string guitar) and along with playing in the school bands played in a group with some friends during my high school and college years, gave it all up to become an engineer. My ex-wife was a soprano and her mom was a piano teacher so been around music for a while.
Interesting conversation here. There's something about music and engineering
Back on topic though, one data point that I would like to add from my experience so far with Jot (w/DAC) is that it seems to have mellowed down quite a bit (either burn-in or my brain-burn-in) after one month (about 15 hours on-time everyday). I sometimes find myself looking for that edgy-ness that I heard at the beginning. But when I switch back and forth between my Crack and Jot, it does have more top end.
Another thing I found is that I have to really crank up Jot to drive my K240 600ohm. For this, Jot pre-out to Crack does a wonderful job.
Cheers.