The Music Collection... sigh

I have once again reached a crossroads in the music collection problem.  I'll spare you the detailed history (which I'm sure you have your own version of) and just give you the current situation... in order of "possibility I'll listen to it."

1. iPod : I love the device, it works in my car for my 15min commute, I listen to podCasts, but I still hate iTunes. 

2. mythTv : this is the families main center for entertainment: we watch DVD's, TV, downloaded content, and I've started ripping a few CD's to it so I can play them through the slightly better speakers.

3. Portable USB hard drive: This is probably my biggest collection - and I copy it to my work machine periodically, but I rarley listen to it.  Phil at work is really good at spinning some good stuff so I let him be in charge or the airwaves at work.  This collection is completely unorganized - no tagging, lots of low-bitrate-mp3 and probably a few songs I would NOT want the children to hear

4. CD Collection: Suzy did a great job of putting all our CD's into folders, getting rid of the cases (not the inserts, just the plastic boxes).  If I had to guess I'd say about 1/5th of that collection is included in the above listed collections.  At some point I will break down and rip it all, but not until I'm sure the effort will not be wasted.

5. Various Storage: This is the worst managed collection - the laptop hard drive, Suzy's old hard drives, some hard drives in the basement not hooked to any computer, some FlashRam in the palm held sutdio thing Suzy got me - possibly this is the most unreplaceable stuff - things that I won't be able to find - or things that are actually original that I recorded (me, the kids, crappy quality, but high sentimental value)

So that's the problem... and I'm thinking I better come up with a solution soon - becuase I want the kids to be listening to music as much as possible, and I know that the house feels happier when there's good music playing.  My brother-in-law John (a major audiophile) has a great collection of CD's and Vinyl that he plays constantly, and I'd love to be able to spend some time with his collection and get a copy of it for myself while also providing him the ability to play it all anywhere anytime.

Sorry for long post, thanks for sticking with it.