The good news, grm, is that we are on the verge of a music revolution that young people like yourself will enjoy and old folks like myself can get a taste of today at far greater cost than you will ultimately need to pay.
I have a musicvault m7 running Roonserver into a PSAudio Directsream DAC. I have subscriptions to Spotify, Pandora and Tidal HIFI. I also have lots of downloaded hi resolution files as well as ripped redbook CD on the 3 terabyte drive of the M7 (as well as a full vinyl system which I will not get into here). I realize this system is well beyond the means of a college student (well into 5 digits) but as I said the cost of these systems is coming down just as your means are, presumably, going up. In the future everyone will have a music server at the core of their system which will stream music and coordinate it from other sources, like a preamp does today.
First let me say that Tidal HIFI is far and away better than what you can get on Spotify and Pandora for sound quality. I have these other two services simply for other features they offer.
A good quality system for you to consider on your budget would be Tidal HIFI (web version, no need for Roon subscription yet), a basic music server (build one from a Rasberry PI or use your PC), into a good USB DAC like the Dragonfly, into a good headphone amp (I built a Bottlehead tube amp but you might need a device that works with lower impedance headphones than my Sennheisser HD580's).
As you upgrade you can get better music management with tools like Roon, a better music server, DAC etc....
