For what it's worth, when I had to solve the same problem that Roger is tackling, I ended up punting to the cloud, uploading everything to Google Music (which just barely fit under their 20k file limit), and paying for the "unlimited" monthly service on top of that so I'd theoretically never have to buy CDs ever again.

It took days for everything to upload, and this leveraging my work machine with its gigabit pipe to the Internet -- this process runs nowhere near line speed, and you're limited to MP3 as the sole file format they support, although they're perfectly happy with high bitrate MP3s. Since I'd previously ripped everything to Apple Lossless, it wasn't a big deal to do the conversion. The total size of the full MP3 dataset is roughly 130GB, also fitting now into a flash stick costing $40 and suitable for various automotive uses. (The future!)

And in the end, it really does work. I have an "offline" button on my tablet, allowing it to cache my collection for when I'm on an airplane. I have the Chromecast interface at home, easily driven and searched via tablet or phone. And at my desk, the browser interface does the right thing.

Honestly, my only complaint is that they don't really have a decent concept of a "family" mode, wherein I can hook my wife's and daughter's phones/tablets into my account, allowing them access to our music. All you can do today is add 'dwallach@gmail.com' as an account on their devices giving them full access to everything (mail, calendar, etc.). That's fine for my wife, but it's decidedly not fine for my daughter.