AutoSync Removable Media

[anonymust]

I Just cant seem to get this to work well.

I have an auto playlist that does the following (see image bellow), that basically shows me my recent high rated songs (based on the time-stamp edit) so I can sync new songs to my iPhone* ...

*Note: I do not auto-sync my iPhone from this playlist, but I just use it as a list/view to the music that I liked recently and/or changed to a higher rating

How Do I set this up? With the following points in mind!
If I sync it from the playlist it doesn't sync ALL the files. (Just the files it never synced before {which gets me to question, does MM log what files it is syncing?}

For example.
I auto-sync the USB on Monday-FEB-14 @ 10:00am ... 20 songs are synced (with the last time stamp {track with 4.5/5 star rating} is Sunday-Feb-13 @ 9:10am)

Tuesday-Feb-15 @ 9:10am Listened to tons of music and rated a few songs 4.5 and 5 starts (these are not added to the autoplaylist in the picture above)

on Wednesday-Feb-16 I deleted all 20 of those songs, because I needed free space on my USB.

Later that same day (Feb-16) I plug the USB into my computer.. I do not want I to resync the 20 files from Monday-Feb-14 (because I deleted them), but skip those and sync all files that have a time stamp newer than Sunday-Feb-13 @ 9:10am


This took alot of explanation ( i know) Im sorry but its full into detail!

[Lowlander]

Auto-Sync knows what was synced before and skips those songs already on the device. If you delete files of the device they get re-synced unless you remove them from the sync list.

If files that you changed the rating on don't show in the Auto-Playlist they may not have a changed Timestamp. This would normally be the case if the ratings weren't saved to the tags.

[anonymust]

Is there then a way I can set up the auto-sync to only sync ONLY say 2GB of music or no more than 100 songs?

[Lowlander]

If you sync a Collection you can set it to sync random subset and have it reserve free space. I personally sync Auto-Playlists which can be limited to x files or x MB.