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I think the biggest hurdle to ripping is just getting past the thought process! It helps to have a solid plan first, and have your tools all in place (software, ripping hardware, storage, etc.). And then once you start, the process is automated enough that it's just a matter of swapping discs in and out when you have a spare hour or two of computer time to work with.
What I would like to see invented is a machine with a big spindle sticking out the top of it. You would just stack your disks on that spindle, and the machine would just load one at a time off the bottom of the stack, saving the content of each CD or DVD or BluRay in a playable format on a giant hard drive array. Digitizing your music is just too much of a pain in the butt if you have limited spare time to sit in front of a computer and just wait.
The part I hate most is fixing all the metadata to my liking.
Just to update--I compiled a stack of CDs from miscellaneous audio boxes of mine, along with a couple of stray box sets, and ripped them with the dBpoweramp Batch Ripper. Once I got the metadata format to my liking, it was almost no work at all to rip through 40+ discs. It took me about an hour to maybe do 30-ish...? That was spread across two CD drives in the computer, working simultaneously. Whenever it hit an error with the metadata, it would pause and pop open a window. Just to save time, I would put in artist and album title, so it would save into a proper folder, then fix it up later with MP3Tag.There are some other multi-disc units out there that can rip with dBpoweramp Batch Ripper, but some I've noticed take a bit of tweaking to get right. Fortunately, dBpoweramp seems to have a guide online which gives suggested settings for some of those units, so they will work properly.