I did a quick estimation of all my CDs and apparently I have about 1100 of them. And probably 500 vynils or more.
Of course it's not all made of albums. There are a lot of singles. But I estimate the average duration of 40 minutes... So after a quick calculation, I would need approx 300GB of space to store my music losslessly. This is already possible with current hardware technology. The problem is to chose the codec and the container... For the container of course it has to be Matroska ;) But for the codec I think the WavPack hybrid mode would be ace. This way when you need to move data on a smaller device you only keep the lossy part (somehow transparent) of the date (100GB should be OK at 256kbps). Unfortunately it's not well supported on handled devices or much players (like DirectShow or QuickTime). Hopefully it will change soon thanks to our team :)