Jawaburger

Sadly there are several speaker manufacturers that sell speakers that cost twice that, if not considerably more. Wilson and Focal are two off the top of my head.

dB PowerAmp definitely has a Mac version

I assume you did not go to their website. They have a Mac and a Windows version.

I just wanted to mention that you can easily use a Windows based PC, or even a Linux machine, since you did not specify that you already owned a Mac. You do not need an Apple computer to play music. If you already have a Mac, then that is cool, and many people use Macs, especially the Mac Mini. But if you already have a PC, you do not need to change that. If you want specific advice on hardware, you should provide a budget, since DACs for example, can cost anywhere from $100-$100,000.

I know it is a rarity on today's flat screen TVs, but if you have an analog stereo output on the back of your TV, try comparing the audio from that with the optical out.

TVs often put out a 5.1 surround sound signal from its optical out. I am not sure what you are watching/listening to when you are using your 2 channel headphone amp on your TV, but perhaps (wild speculation, of course) you are having such a difference in volume because you are missing a lot of the audio information. It may be that your headphone amp is not giving you the information that would normally go to a center channel.

Most agree that having a sturdy cable with proper shielding and solid connectors is a good thing, and your proposed budget should satisfy those needs. You can get some pretty solid cables without spending a lot of money. Monoprice and C2G make some solid cables for around $10 (not sure of dollar to pound conversion), depending on how long of a cable you need. The AudioQuest cables will run from $20-$50 or more, depending on what line and what length you need. I use some AudioQuest cables in my system and I like them. Hopefully others will chime in with their advice and ideas.

You can try Audio Quest. They sell a variety of cables at a variety of price points. I am sure you can find one within your budget. Whether it makes a difference is contentious.

The easiest way I know of is to take audio out from your preamp/receiver into the mic input on your computer using RCA->3.5mm adaptor and use Audacity or Windows Sound Recorder to record the incoming audio. You can also try using a phono preamp with a USB out, like the NAD PP3 or the Rega Fono Mini, both of which have a passable ADC. I know the NAD comes with software for the record ripping; not sure about the Rega. Those are the easiest and cheapest routes, though maybe not the most desirable when it comes to quality.

The best advice is to listen to a few options in your price range and then pick the speakers you like the best. Speaker selection is hard to advise as some people will hate the same speakers that someone else loves. If you do not have a store near you that sells speakers, you may have to rely on anecdotal evidence from others.

Are you ripping a lossless file from the CD?

From my experience, it is actually harder to find a current DAC with no volume control than it is to find one with a volume control.

From what I have seen/heard, most of the songs during these show are fringe/alternative pop songs. They are not really mainstream because those would cost too much money, but they are known enough that I recognize some of them.

Really? That surprises me, because I am able to watch HD videos from Netflix with my 10Mbps internet speed. I personally don't stream at home as I find my CDs and digital music files have a better sound quality.

If you have a DVD recorder you can take the video out from the laser disc player to the input on the DVD recorder and copy the movie to DVD. You can then use a variety of software to rip the DVD to your computer. I have done this with many VHS tapes and home movies. If you have a video capture card on your computer you can go straight to your computer from the laser disc.