It'd be a lot easier to get a "personal" end game setup off the rip these days.
My first setup was a "Zero" DAC/AMP off Ebay in 2008, paired with Grado SR-80s. The Zero amp was something some dude in like hong kong was building. The actual amp was nothing fancy, but it used an opamp that was super high end for a budget component way back in the day.
You're right, it's definitely an expensive hobby and you can spend a lot of money chasing that dragon so to speak. I was lucky in that I got something that sounded very good to me with my first set of purchases, but I was obsessed for a while with reading every detail about potential purchases.