help me "face the music"?

Hello audiogoners,

So for years I have been clinging to my CDs. But the fact is my need for music will soon surpass my ability to store them, and also my partner and I share one music collection between two houses in in two cities that are two hours apart. So I am now facing up to the fact that it is time for me to start thinking about going to a computer based system. I’m starting from scratch and have been perusing advice here which is helpful but also overwhelming.

I have a Macbook Pro. So far this is what I’ve gathered:

-I need to put itunes on that computer and also some software so I can rip my CDs in ALAC format. Is that right? Or is some other format preferable? And is JRiver for apple my best bet? Or something else? (My cds are not SACD but just regular cds).

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

-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?

-Is there a disadvantage in terms of sound quality in using the ipod as the source (rather than the laptop?) Will ALAC files also play on the 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?

-In terms of components, what are some entry level but good places to start? Seems like the Rega Brio R and the Rega DAC are well thought of. Would a NAIM Uniti2 or something like it be comparable or is it preferable to have a separate DAC?

-Are some speakers better suited to digital than others? Most likely, I need a small sealed box and have my eye on the Harbeth P3esr but is it a waste to use this speaker with files playing through itunes? (I hope this question isn’t offensive…I’m really a novice!) Are there speakers that are better suited to this application? Neat Iotas, for example?

-Thanks for any guidance!

MC