How Do You Live The Audiophile Life

This room has me losing the game before the opening kickoff. A lack of decorating options that forces the speakers too close together and aimed directly at the dining table or empty wall/window space, leaving all the comfortable sitting positions in front of one speaker or the other. 
Plus, the room is too small to allow for any serious rearrangement. When I got the new NAD stuff, the clarity demanded that I give the speakers a few more inches of distance from the wall behind them. A few inches! All of my books had to go to make room.

Every year I ask the kids if they’d like to move to the suburbs. Their own room, a yard, room to run! Every year they threaten to beat me up if I even think about it.

The serious audiophile would get rid of it all, put one chair at one end, the two speakers at the other (one blocking off the hallway), forming the perfect isosceles triangle, and the hell with everything else. If the 16-year old boy would have to go, it’s worth thinking about. 
The biggest joke of all is how much I pay for this place. Ah, NYC living!

To the OP...

The best advice I've ever heard (and I wish I heard this years ago), was:

It all sounds fake. Just pick your favorite kind of fake.

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