1. What is the best software?
For Windows, JRiver Media Center 18, of course. MC can rip in a high-quality, secure mode, which is functionally the same as other "advanced" rippers like EAC. It should serve your needs well.
2. Are their specific settings that I need to use?
That depends somewhat on your needs, but here's what I'd use:
Options > CD, DVD, & BD > CD Ripping > Drive > Copy Mode: Secure
Options > Encoding > Encoding For: CD Ripping (the drop-down at the top)
Encoder: FLAC Encoder (leave everything else at the defaults)
However, you may not want to encode to FLAC if you want to use the files on your OSX box with iTunes. JRiver MC will be coming out for OSX here before long, so that problem will be eventually solved. However, if you want the most cross-compatible format, you should maybe stick with MP3. You can easily "max out" the MP3 settings by selecting the MP3 Encoder and then choosing VBR Target Quality Extreme.
Alternatively, you could:
1. Rip to FLAC and then make MP3 "sidecar" (stacked) versions of each file for use with portable devices and in iTunes.
2. Rip to ALAC (Apple's Lossless format). This is supported much better by MC now, but you'd have to ask someone else for the details.
3. Rip to WAV, which wastes a bunch of space, but it is identical quality to other lossless formats, and should be universally playable.
3. Does it matter if I use my computer's DVD/CD player or is it best to use additional hardware/cables?
No. Use MC in Secure Mode. This verifies the rip bit-by-bit and re-reads until it gets it right. It can also generate a quality report. If the rip was less than 100%, then you probably have a scratched source disc beyond help, though trying a different optical disc reader can make a difference.
The rip is NOT analog, so cable quality doesn't matter. It either works or it doesn't. The only time you'd need to worry about this is if you're getting
all failed rips, and then you might have a broken cable.
4. Is there such a thing as a bulk ripper for high end audio that works with great software?
Well... There are devices that will auto-load optical discs (
the Nimbie is one). It should work with MC, but that is a quite expensive option (and I don't know if it is tested). There are commercial ripping services online where you can mail them your discs and they'll rip them and send the files/discs back to you starting around $1 per disc. That might be roughly a wash with buying something like the Nimbie, and of course, it'll still take a bunch of time/effort to get the hardware set up and then plow through them.
You could also just buy a few extra Optical drives for your PC and rip 3-4 discs simultaneously. MC will use them up to the limit that your CPU can handle, I believe. jmone can chime in here... I know he rips multiple BluRay discs simultaneously with MC all the time and should know the details.
For commercial ripping services, you'd have to look for one with high quality standards (using a secure rip and providing the secure rip report for each disc back to you), but I imagine there are some if you look.