[Letitroll98]

Tom's Guide had this article about building a $500 system, wadda ya think?

https://www.tomsguide.com/audio/speakers/how-to-make-a-home-stereo-system-for-less-than-the-price-of-one-sonos-speaker

Spoiler it includes a Winn Amp and Polk speakers, there's also a headphone system option.

[Mag]

Realisticly I don't think I could do it. For starters I don't buy used, because you don't know what you are getting and item maybe stolen and I don't buy stolen goods.
 So the cheapest way I can think of doing it is to buy a laptop. You can then using Bluetooth use wireless earbuds. Or you could buy a Bluetooth headphone amp and connect that to a Receiver amp and have the amp connect to speakers. Anything half decent that I would use would be in the neighborhood of $1000 Canadian at least.

[yamaha626]

I think it was an OK article. Personally I wouldn't do the Wiim amp and couldn't care less about having headphones but my sub $500 system would probably start with a used Receiver (thinking an Outlaw RR2150) and some used speakers.  If I had enough money left, then I would get a cheap dvd player for listening to CD's.

[I.Greyhound Fan]

I think that it is a good starter system.   I might look for better speakers though.

Nothing wrong with going used.  I bought my Pass amp and BAT preamp used.

[AllanS]

We actually built $500 system for one of our kids over Christmas and his b-day a couple of years ago.  It did include a WiiM amp and Polk Audio Signature Elite ES 10 speakers both new.

If you’re patient and buying local or from trusted forum members you could find a decent used integrated and bookshelf speakers.  Sticking to new I’d be looking at Accessories4less for an integrated.