help me "face the music"?

1. You do need iTunes. It is a file management tool, ripping tool and playback software. It has the ability to import (rip) your CDs into several formats. First I recommend you use a lossless file format (ALAC, WAV or AIFF). ALAC is compressed with the only benefit that of saving space (size of the files). AIFF and WAV are uncompressed. You will want to tag (add metadata) to your files and ALAC and AIFF are better for that purpose. A very popular compressed lossless format is FLAC but not supported by iTunes in and of itself.
2. I use another software for ripping on Mac, XLD which is a free app. It offers the benefit of AccurateRip
3. There are several software playback tools that work in conjunction with iTunes. I use Pure Music and Audivrana. JRiver For Mac is another option. It is a great tool providing library management and playback. It currently does not support ripping on the Mac side.
Back up, back up, back up. Whether you decide to store your files on the internal drive of your MacBook or on an external drive have one or two drives available to keep back ups right from the beginning.
4. The connection you suggest from your MacBook to a DAC to your audio system is correct.

I suggest you visit Computer Audiophile online. Find the FAQ and the CA Academy. There is a wealth of resources and information there.

The Mac SuperDrive should be fine for the work intended.

A general rule of thumb is if you are using external drives have those connected to a different bus/connector than your DAC. So if your DAC is connected via USB try to use FireWire or thunderbolt connection for the external drives.

The Rega products you mention are generally well thought of.

Buy Fidelia software rip your CDs, get a decent DAC and be happy.

Since you and your partner reside in different locations but share one music collection, you may find a solution that incorporates network attached storage (NAS) to be very appealing. That way all of your music files can be readily accessed at any time from either of your locations. Synology, a manufacturer of NAS devices, gets very good reviews.

I need to put itunes on that computer and also some software so I can rip my CDs in ALAC format. Is that right?

Correct.

Or is some other format preferable?

.wav format is superior, however you lose the tags and album art. If you only care about sound quality rip to .wav.

And is JRiver for apple my best bet? Or something else? (My cds are not SACD but just regular cds).

I recommend either Amarra or Audirvana. Both work with iTunes.

-Can I use the Mac “superdrive” to burn CDs or is another piece of hardware preferable?

you can , but it is better to use an extern high quality USB drive with C2 error correction capability.

-Then I use a digital cable to connect the Macbook into a DAC and that runs into the amplifier? Sounds simple. Is there anything I am missing?

you can, but it will not be pretty.

A better result is to move the Master Clock out of the computer and into an external device that can deliver lower jitter. The device of choice is a USB converter, such as the Off-Ramp 5 or Diverter HR. The jitter of this digital source is MORE IMPORTANT than the DAC.

http://www.empiricalaudio.com/products/off-ramp-converter

http://www.empiricalaudio.com/news-and-reviews/off-ramp-converter

This connects with a USB cable from the computer to the USB converter. Then coax from the USB converter to the DAC. The DAC can be a SS receiver or SS processor as well.

You can also just buy a USB DAC and use the USB converter inside that DAC, but it will never be as good as the external USB converter powered from a high-quality independent power supply.

-Is there a disadvantage in terms of sound quality in using the ipod as the source (rather than the laptop?)

No, because the master clock in the iPod is not that great. You can improve it by using a digital docking station like the pure i20 ($85 on Amazon) and then drive that to a reclocker like the Synchro-Mesh to reduce jitter. If the Synchro-Mesh is powered by a good supply like the Dynamo, it is world-class, however the USB converter will still be a bit better.

http://www.empiricalaudio.com/products/synchro-mesh

http://www.empiricalaudio.com/news-and-reviews/synchro-mesh

Will ALAC files also play on the ipod?

Yes, even .wav files will play. This is what is on my iPod.

-If I also wanted to use an internet radio service like Sirius or Sonos, is there any way to have that sound relatively good?

Just achieve the lowest jitter possible by using an Off-Ramp 5 or Synchro-Mesh and it will sound great.

Steve N.
Empirical Audio