Going to rip 2000 cds. Which software?

At 63 years old I've decided it's finally time to make the move to a digital library.  I've spent hours and hours on this forum reading about servers, streamers, music servers, nas systems and modded Mac Minis.  I'm more than confused.  I'm pretty much ready to just buy a new transport and be done with it. 

But.... I play "cuts."  I hardly ever play an entire record or cd and would like the ability to choose what's playing from the couch.

I know that the first step is ripping cds.  I have a couple of questions;

1.  Which software should I use?  I am concerned about speed and indexing.  I'm a jazzhead and have quite a few recordings by the same artists that have recorded multiple versions of the same tune.  I want to make sure they are indexed properly.  I would also like a program that doesn't take all day to make a copy.

2.  I can use either Mac or PC.  I would prefer Mac but would use a PC if it is more future proof.  I have a Macbook Air and a PC laptop and both have dual 2 terrabyte external drives.

3. I would also consider a Music Server with a nas rig.

If I do a music server with nas I'd like to keep the price around $2000.

Thanks to all of you.

--Bob