Ooooo. This is like detailing. What you buy to use isn't nearly as important as how you use it. You can spend $50k and that won't matter if you stick one B&W behind the couch and the other in the corner.
1) If it sounded good 50 years ago, it still sounds good today. Sure, there might be something better today; but that doesn't mean that outdated equipment isn't good. If you don't believe me, you've never giggled while listening to Dyna PAS3/ST70 and Large Advents beating out an old Stones album through a Grado tonearm & Shure B cartridge on a Rekokut TT. That stuff was live as hell.
2) The suggestion for used equipment is a valid one; you can get some outstanding bargains. The Advent 300 receiver is always available. I've picked them up for $10 (but ~$100 is more typical). The amp itself is ok, the pre-amp is the revered Hafler circuitry. The FM tuner is one of the best ever. There are other brands, but this is one of my pets. I have a soft spot for this one. (A quick ebay check shows a current range of $78-$175.)
3) Then get the best speakers the rest of your budget will allow. I haven't shopped that price range for a long time, but I recall Paradigm has a nice product. There are others, do a bit of research.
4) What's going to screw you is that bass requirement. THAT is the most expensive part of a high quality system to get right; what you are setting up as a requirement can cost thousands all by itself. Especially since you are going to be listening mostly with compressed source material, my recommendation is to concentrate on the more traditional values of balance and imaging. The bass will be there, if you choose your full range speakers wisely. I have invested many, many dollars into high end audio, and I still haven't even bothered to try to integrate a subwoofer. (For those who are interested: tubes and electrostatics, with 50/50 vinyl and digital).
5) Since your source material is going to be a computer hard drive, I'd recommend for your first upgrade a high quality USB DAC (digital to analog converter). Headroom makes one for $300, but there are others that are good (I know Headroom's is USB). That will make a world of difference. The DAC in you computer is usually really cheap; computers are under a lot of price pressure, and audio quality isn't even on the list of things most users are looking for.
6) The biggest difference that you can make in what you hear is PLACEMENT. Your room, your environment is part of your system, and the best thing is, it is the part of your system that makes it sound the best and it is also the part that is free! The subject isn't all that complicated, but it is a bit too wordy for a post on an internet detailing forum. But another great thing is that your resources, in this digital age, are much better than ours were 15 and 20 years ago. Google it. Start with "the rule of thirds" and make changes from that based on what you hear. You will find a sweet spot. Speakers can be placed to improve bass perception, to widen or shrink the stereo image, and to brighten or dampen peaks and valleys in the sound. Plants, pictures, blankets, wall hangings, and rugs can do wonders. And those are either things you already have, or things that both add to your environment and improve your sound.
So to sum: a high quality used receiver (Advent isn't the only good one; Onkyos and Yamahas were pretty good, too) and the rest of your budget on the best speakers you can afford. First upgrade, a high quality DAC. And make your listening room or area a place that feeds your goal af sound reproduction and enjoyment.
It isn't really going to be what you buy, it's going to be where you put it when you get it.
Tom,
who has been missing in action lately.