I'm currently using a Schiit Modi for my DAC and a Schiit Vali 2 for my headphone amp. They seem to work pretty well to my ears, whether they're driving my Meze 99 Classics headphones, or the PreSonus Eris E4.5 powered speakers.
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.
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.