Alternate "sync random subset" method

[FeldmanSkitzoid]

I have a music collection that takes up more space than my portable device can hold, so I use the "sync random subset to device capacity" feature when performing a synchronization. However, I recently had an idea for how to make this feature more user-friendly.

My "math" or my understanding of what's going on may be wrong, but I hope I can still convey this idea effectively enough.

How it works now (as near as I can tell):
1. I activate a "sync" for my device.
2. MM determines which files to delete from device.
3. MM determines which files to sync to device.
4. MM deletes the files from the device.
5. MM copies files to device in alphabetical order (more or less).

If I have 4000 files on my computer, and my device can hold 2000, about half of the files will be deleted from the device in Step 4. But let's say the sync freezes, or I have to disconnect my device midway through the sync. Now I only have 1000+ files on my device.

This is all working as intended, but problems start to crop up with repeated disconnects. If ~50% of the files were removed from the device the first time around, ~50% of what's left will be removed the second time, and so on. This becomes annoying, especially if you're having trouble syncing (thanks to DRM or something).

Further, if Step 5 only completes partially, you wind up with a lot of songs from the beginning of the alphabet getting synced, and nothing at the end. You get your AC/DC just fine, but no ZZ Top.

The Point:

Here's my suggestion for an alternate "sync random subset" method. There could be some very good reasons for why this isn't feasible/possible, but here it is:

1. I activate a "sync" for my device.
2. MM determines which files to delete from device.
3. MM determines which files to sync to device.
4. MM randomizes the list of files to delete from the device.
5. MM randomizes the list of files to sync to the device.
6. MM begins copying the files to the device. If the next file on the sync list can't fit on the device, MM deletes the first file from the delete list. Effectively, MM frees up space as needed, rather than all at once.

This would hopefully solve the problems that crop up when you don't finish a sync: you still wind up with a device full of music, and you still get music from the end of the alphabet.

Anyway, I hope that was clear enough. Thanks for your consideration!