1. Yes, length matters for USB when over 15 feet (the point of USB signal degradation). Kimber makes a great USB cable, but I've never used one longer than a few feet for audio.
2. iTunes works fine for most people. If you are worried about read errors, run your ripping software it in "secure" or "paranoid" mode (language depends on the software). The speed depends mostly on your CD drive and it's capabilities. If it's a combo CD/DVD r/w then it will likely be slower but more accurate. If speed is that important, get an external CD only drive or consider a ripping service. If you have a large library (more than 500 CDs) a service can be well worth the time/cost factor.
3. Technically, vinyl resolution is lower than even redbook CD, but that doesn't mean the higher resolution won't provide some benefit during the recording process. If your equipment supports it and you like the sound of it, then definitely give it a try.
4. The Benchmark products you mention look promising, but that doesn't tell the story of how you intend to generate the analog signal to begin with. Are you happy with your table, cartridge, and phono stage to the point you can live with that sound in digital format? I would Google around and see if you can find a service that would do this as well. The time commitment alone makes this sound daunting.
One last comment. Given the amount of money you are prepared to spend for the DAC and the possible ADC, give serious consideration to getting a computer that is 100% dedicated to being an audio server such as a mac mini (best option), laptop, Apple TV, or a Dell Studio Hybrid. You can have any of those for at (or under) $500 This allows you to put the computer closer to the system (shorter cabling) and optimize the computer for audio.
Good luck, and have fun!
2. iTunes works fine for most people. If you are worried about read errors, run your ripping software it in "secure" or "paranoid" mode (language depends on the software). The speed depends mostly on your CD drive and it's capabilities. If it's a combo CD/DVD r/w then it will likely be slower but more accurate. If speed is that important, get an external CD only drive or consider a ripping service. If you have a large library (more than 500 CDs) a service can be well worth the time/cost factor.
3. Technically, vinyl resolution is lower than even redbook CD, but that doesn't mean the higher resolution won't provide some benefit during the recording process. If your equipment supports it and you like the sound of it, then definitely give it a try.
4. The Benchmark products you mention look promising, but that doesn't tell the story of how you intend to generate the analog signal to begin with. Are you happy with your table, cartridge, and phono stage to the point you can live with that sound in digital format? I would Google around and see if you can find a service that would do this as well. The time commitment alone makes this sound daunting.
One last comment. Given the amount of money you are prepared to spend for the DAC and the possible ADC, give serious consideration to getting a computer that is 100% dedicated to being an audio server such as a mac mini (best option), laptop, Apple TV, or a Dell Studio Hybrid. You can have any of those for at (or under) $500 This allows you to put the computer closer to the system (shorter cabling) and optimize the computer for audio.
Good luck, and have fun!