A: Well, you got to take into consideration that I'm a certified senior citizen, so I have to start counting my music purchases around 1970 and . . .
B: As the bulk of my gear was bought real cheap at thrift stores and the like, I now have more sunk into headphones than anything else. Total cost of my gear (other than the headphones) is in the neighborhood of $500 and while it isn't as high end as what your using, it's not too shabby either. That $30 pair of Infinity Primus towers is one hell of a deal.
I doubt I'll stream, for various reasons including my experiences of the signal having dropouts. I've already got lots of CDs and intend to have more. Different priorities, just like anyone else involved with this hobby.
Finally, my playback gear or recordings do not have to be "perfect" in order for me to enjoy music. Some of my favorite classical music recordings are Willem Mengelberg's 1920s recordings of the Concertgebouw.