Media player

Okay, so you're downloading/adding files to your iMac and putting them on your stick for playback through your Universal.
I'm not sure how you fit 5,000 apple lossless files on a 256mb stick, when that file type is about the same size as Flac files? Do you mean those files are on your iMac, and you move over what you want to the stick?

The 256mb USB stick has a copy of what is on the Music folder on my iMac. I also have use Apple's automatic backup feature (Time Machine) which backs up what's on my hard drive once per hour.

At the risk of tempting the fates, I think I am covered.

Lse,
Sounds great, but don't you have all those files on your stick backed up somewhere?

I have a universal player and have my entire 5000 song lossless music collection along with the 2 dozen 24 bit albums on a USB stick and I can access everything in seconds. No fuss.

I use a NAS (Network Attached Storage) for all of my music files. This is simply a big hard drive that plugs into your home network.

Working with the NAS, I have a small Computer with J. River Media Center installed. This too is on the home network. The Media Center software on the computer plays the files from the NAS. The computer is connected to the DAC of my audio system for playback.

On my iPad, I have an app called JRemote. This interfaces with the software on the computer, so I can play and control the music that way.

The J. River Media Center software handles, music, videos, and photos. I don't do anything with music videos, so have not worked with those.