How do we live the "Audiophile Life"? Well if you have to ask.....
Actually, we all have more money than you do. So much in fact that we can afford capricious purchases of 5 figure equipment, just using pocket change.
I hope you realize I am joking.
We all started somewhere. If we started young, it was likely with limited resources. If we started older, we likely had a base of HT or other generic equipment as a foundation. Regardless. We all had to learn what we wanted, learn how to evaluate sound in the abstract, and how to determine if differences are true improvements or just the novelty of something new. It makes no sense to dive into the deep end and spend large sums of money to start your journey.
You reference living in NYC, and have a multitude of dealers in relatively close proximity. GOOD. Any reputable dealer will welcome your visits as you learn. A good dealer understands that education is part of the high end sales process. You live in a large market. As a practical matter there is a large and dynamic market for used equipment in the 5 boroughs. Craigslist, Ebay Local, Facebook Marketplace are your friends. As you learn, you will able to sample just about anything, and likely be able to resell along the way to break even- your only investment becomes time. Don't be afraid to ask questions.