Decide what level of fidelity and "sound characteristics" you want and choose the DAC first - that will help define the rest of your solution.
I personally enjoy the Transporter (uses a "Miracle" DAC) and people rave about the ModWright Transporter. I heard it briefly at the Rocky Mountain Audio Festival a couple weeks back and found it almost as nice to listen to as a great turntable. That would keep things simple and provide shortest signal path (and fewest cables).
If you go with a computer solution, I haven't heard better than the Wavelenght asynchronous DACs. They have a special USB connection that allows the DAC clock to run the digital stream instead of the computer and the resultant reduction in jitter helps significantly. At the RMAF two weeks ago, this was the "affordable" room I thought sounded best and most of it traced back to the asynchronous DAC in my opinion.
For USB cables, Kimber makes a great bang for the buck cable (about $50 US for a 6 foot). Lengths over 15 feet (where USB signal degradation becomes problematic) get extremely expensive. With a computer solution, definitely use USB as most optical or coax adapters on computers are compromised at best (and expensive to do well).
Wireless transmission of data files has no impact on the sound. In the computer realm of data, bits are bits. Fidelity is impacted when a) the file is transformed into a digital music stream (accurate?), b) when that stream is transported to the DAC (jitter?), c) during the D/A conversion process (more jitter), and d) any subsequent transporting of the analog signal to your amplifier (coloration, distortion). The conventional wisdom of "shortest path being the best" is almost always true with Hi-Fi, and this is no exception.
My advice to most people is this; if you like toys and fiddling with stuff, do a computer oriented setup and have fun with it. If all you care about is ease of use and good fidelity, get a Transporter (ModWright if you can swing it) and be done with it.
Finally, be aware that there are many high end hardware makers entering this sector in the very near future. I saw the new PS Audio DAC a couple of weeks ago that uses I2S for data transport and that has potential to be a real game changer if others follow suit.
Good luck, and enjoy!