Honestly the $500 barely gives a fair shake to trying the real/true audio waters. Sure you can do it at the big boxes, or DIY, or by rummaging through vintage stuff and taking your chances that it works, will keep working, or works well together.
As an adult with a real job, I can understand your position. But remembering what it was like to be a young 20-something student getting a MS or PhD and not having a substantial income, your post comes off as audio snobbery. Even the little guy wants to think they've got a good starter system. And they should have that right.
I think the key here is $500 to $1k dollar increments. Buy used (or "vintage") gear, and experiment with DIY.
A perfect example is the path I chose. As an undergraduate summer job, I sold audio at a (blue) big box store. And during that time, Arnie Nudell's Eosone line was introduced, and I was able to get their flagship speakers at 75% off. Later, in grad school--a fellow audiophile was in financial need, and we agreed to swap my Pioneer HT receiver and about 250 bucks for his Rotel 980bx amp and Rotel 950 pre-amp. Definitely, a great place to start--as it was Stereophile (Stereopile) class B. I use that amp as my back-up am even today. And since I had a decent high-current amp, I was able to save up and get a pair of Acoustat 2+2s for about a grand a couple years later. A couple hears after that, I was able to pick up Frank's Omega III 440HC for another grand (used). About a year later, I picked up a used OmegaStar pre-amp (SL). Forgot what I paid for it, but it was between $500 and $1k. And since then, I've upgraded the Omega III to the current OmegaStar.
And I was able to do this before I finished my degree. Not bad for a "poor" student, who researched his options, was patient, and made calculated long-term decision. Acoustat 2+2 full-range electrostatics, Frank's OmegaStar 440HC and OmegaStar pre-amp.