Less is more, a signal path is unlikely to increase in quality as you add stuff to it.
Pretty much what Brocklambert said. A good way to look at things is by going through your signal chain and making the best (quality/financial) upgrades. Regarding your setup I'd go down the list like this:
1. Songs. It all starts here. The most basic upgrade you can make is by playing WAV files. You can have an amazing sound system, but it will sound crappy if the song is crappy quality. Avoid MP3's if possible. This is honestly one of the easiest upgrades to fund, and is overlooked a lot.
2. Sound Card. In your case, the VMS 2. Trickier since it's built into the controller. In terms of the overall sound quality, the increase will be marginal compared to your amp and speakers. I would look into upgrading this when you feel like you need a new controller.
3. Amp. Doesn't look too shabby. Speakers make a bigger difference, but never skimp out on an amp. I would say, upgrade this when you are ready to move onto more powerful and better speakers and need a stronger amp. A good amp is clean and reliable, this is why people stick to certain names like Crown, 'cause they do just that. They may have a bigger price tag but are well worth the investment.
4. Speakers. You'll see a huge range of quality possible here. Sadly, this is also the most expensive area to invest in. Sort of the same story as amps, it's all about quality and reliability. Hard to go wrong with the big names as they've proved themselves up to the task, at sadly, a higher price point.
5. For the sake of it, audio transport. Stick to good balanced connections if possible, but it seems like you're already doing that.
In you case, I'd focus on trying to only play WAV's as an immediate improvement (and a good future habit). Aside from that, it seems you'd benefit the most from some better speakers. Though I realize that's the most expensive upgrade. If you need help understanding anymore of this stuff, don't be shy to ask, I'm a bit more versed on the techy sound engineering aspects.
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