How Do You Live The Audiophile Life

I think it's important to take everyone's advice with a grain of salt, especially the ones that are the most heavy-handed.

I would say that it is important to listen to a few good separates in the shops and also (if possible) at home.  There are too many possibilities so know from the start that you won't be able to listen to them all.  Also, real-world budgets and real-world listening spaces will not achieve the "nose-bleed-high-end-best-of-show" sound that you might aspire to.  Overall, take a test drive on a few components based on reasonable reviews and find what you like to hear (not necessarily what others say you should hear).

In my experience, speakers make the most difference and needs to be tailored to your listening tastes.  However, one needs to be mindful of budget and space constraints (e.g., speakers you dream of may be too big for your space).  Amplifier needs to be matched for your speakers.  DACs need to be accurate.  As for connectors and speaker wire, my ears do not let me hear the difference between decent entry level items and the really expensive esoteric stuff: for example, there was a big difference between crap speaker wire and the cheapest Kimber Kable speaker wire, but I couldn't distinguish between the different Kimber Kable wires in blind testing.

Personally, I wasted a lot of money in my late 20s and early 30s looking for better equipment based on others' opinions (sometimes even letting those other opinions sway me away from what I liked).  Then, I found a reasonable amplifier and a pair of speakers that matched my musical tastes and have been concentrating on the music (that was 25 years ago).  DACs and preamps have been upgraded over time to take advantage of the improving technology (particularly DACs).

Hope you enjoy your journey and the music.

"If the 16-year old boy would have to go, it’s worth thinking about."

Depending on the actual birthday, one more year and you are done with that one.

Every time I visit another city I find the high end audio stores and go for a visit.  Kick their tires and get a line on why they promote the products they promote.  I find it very helpful

Once a performer plays / sings into a microphone, or mixing console, you have lost all truth, all reality, all the accuracy, of said instrument or voice. Recordings are limited, and the playback gear, is purchased, to try to reassemble it, back to it’s beginnings. No matter how much you spend, no matter what you do to your room, no matter how experienced you are, as a listener, the sound, will never be " like the real thing ". So, knowing I am listening to a recording, I stay engaged, and listen to the " playing ", the " singing "......the " performance, the artistry " aspect, of my favorite musicians. PRAT, is a real thing. Dynamics, is a real thing. Fortissimo and pianissimo, are a real thing. Yes, tone is important. Coherence is important. Stage development, is important. These are all part of live, unamplified music. Determine what is most important to you, and if who you are listening to, engages you, and continues, to keep you listening....you are, on your way. Enjoy !

I guess you missed the show I mixed for Jim Campilongo a while back. He uses a Princeton Reverb turned all the way up, and had he been unamplified...well...perhaps somewhat harder to enjoy...