Smile,
Thanks for taking the time to answer my questions. So here's the deal - as I see it at least:
Before we begin to discuss hardware, let's talk about software. The bottom line is that if you want to get great sound out of your PC, you're gunna have to optimize it for audio playback. This usually means combing through the operating system and disabling all of the functions that you neither use or need. Once you've done that, it's then all about selecting the best sounding software that you can find.
If you're running Windows, I'd recommend JRiver Media Player. It's the best sounding software around for Windows (in my opinion), plus, it's very easy to use. Unfortunately, it also costs money. If you'd like to try something free, then I'd use Foobar2K in place of JRiver. Foobar isn't as pretty, but it still performs quite well. No matter what you get, I'd recommend that you also download a piece of software called Fidelizer. This FREE software helps to optimize your OS for serious music listening. You'll need to run it in conjunction with whatever media player you end up using.
If you're running an Apple OS, then I'd recommend Amarra. It's expensive, buggy as all get out, and the user interface isn't terribly well thought-out, but it's the only music playback software for Apple that doesn't suck (in my opinion).
Alright, so now let's talk about hardware.
The Maggie recommendation is a good one, but there are a couple issues with this approach. The first is the price. The Maggie Mini system costs $1500. You're still going to need to buy the components to go with those speakers. Throw in a DAC and an integrated amp that's capable of safely driving these speakers, and you're going to be well above the $2000 range. Beyond budgetary issues, it's worth noting that these speakers were not designed to fill a 14x20 space with a whole lot of sound. They were built for near-field listening. Also, I'm not sure if mini-planars and pop music is a combination that'll work out well.
So with that being said, let's look at some other choices.
Earlier this year, I assembled an affordable desktop rig setup that kicked butt for the $$$. I ended up using an iFi DAC ($300), a Quinpu A6000 MK II integrated amp ($250), and a pair of Dali Zensor 1's ($500). For a 14x20 room, I'd step it up to the Zensor 3's. Anyway, this is an example of a carefully constructed two-channel rig that delivers performance that is way beyond it's individual parts. This setup was chalk full of speed, tone, and dynamics. Given your budget, if you went this route, you'd still have enough money left over to anchor this system with a decent sub.
Anyway, the truth is that the choices are damn near endless. In a way, it's good to have options. Yet by the same token, having such a huge palette of choices can be quite annoying. This is why I asked if you had an idea as to what kinda sound you're looking for. If you do, that'll help us to give you a direction. Anyway, for what it's worth, I prefer desktop systems that gravitate towards the smooth side of the aural spectrum. Why? Because most computers sound ridiculously digital to my ears. And by digital, I mean harsh and unnatural sounding. So given my bias, I tend to build PC rigs that strike a balance between transparency and musicality. I don't want something that's *too* colored, but I sure as hell don't want something that's too revealing either. Not when it comes to PC listening, at least.
Alright, I suppose I'll draw this incredibly long winded and somewhat incoherent post to a close. Hopefully there's something that you'll find useful within this huge pile of text. Oh, and before I forget.. if you end up buying a pair of bookshelf speakers, please don't set them directly on top of your desk. Buy some mini-stands, or make your own. It's all about controlling resonance.

Good luck!