Music manager for a mass storage based music player

Question

I'm a bit of a music buff who has been converting his collection to flac - the process is still ongoing so I have a mix of 320vbr and flac files. I also like being surprised, and have a fairly large music collection. I use a mass storage capable device as a music player and would like a tool that would

1. pick random tracks from a file/folder hierarchy - if I point it at /music, it needs to find files under <root_music_folder>/artist/album/codec/
2. convert them to mp3 if they're flac (so I can save space, and not maintain a separate set of mp3s as I did with iTunes - this can be by location or extension
3. copy them over to a folder until the drive is full, or better yet, I've reached close to a specific user-set size.

Is there anything that would do this?

I'm running Windows 7 and 8 mainly, so I would prefer windows, but I would accept a Linux based solution if nothing else is as good.

I'd like to keep dependencies minimal - I suspect doubletwist does this, but I need an iTunes install, which installs a bunch of additional things I don't need, and the last time I ran it kept suggesting I install Safari. A foobar2000 plugin would rock my socks, since that's what I use as my preferred player anyway. The idea of something portable seems attractive as well, and certainly upvote worthy.

Answer 1

Mediamonkey seems to cover most of my needs.

The free version handles 1 and 3

It allows me to Sync a random subset of files up to the device capacity, and let me leave a certain amount of space free.

The paid version also does conversion based off rules so does 2. Its standalone (though not portable), and dosen't rely on anything else.

As a bonus, it seems to be a competent music player, even doing WASAPI