Greetings!

Let's see...

how are you going to go from 160 gb --> 40 gb

I am not certain yet. I have a favorites playlist that I keep randomized for short trips. That only has about 2,000 tracks, so that should fit on the Pearl.

Most people that I've seen pegging out anything over 120 GB are either audiobook people or they are ripping at a very high bit rate.

Or both...

A more sane average of about 200kbps yields enough space for 1600 CDs.

Actually, that is about right.

I keep putting on full albums whether I like all the songs or not, just so I have them for whatever reason (which I probably wouldn't do on the Pearl).

Same here. Since the car player is docked at the office, I have the entire library here on demand and online.

You can never have too much space...