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[benn600]

I have an idea, does it seem like it could work?

1. I have a NAS with all my media.  I use a Windows computer to run Media Center Library Server (latest version)
2. Set up device synchronization to synchronize my iPhone playlist to a folder in my Dropbox (Apple Lossless audio)
3. Enable automatic synchronization of this device (is this possible? could I do this with task scheduler)
4. Add a script to my Mac that adds this Music folder to iTunes periodically (iTunes will add songs it doesn't have, it will not copy them to its iTunes folder but rather use them from Dropbox)
5. Enable WiFi synchronization of my iPhone, hopefully this can also be automatic and in the background

If this could all work (especially the automation) then the end result would be:

1. I could connect to Media Center from any client and add or remove songs to my iPhone playlist.
2. These would automatically sync back to the Media Center server, which would in turn synchronize and update the export folder (in Dropbox)
3. This would give me my favorite tunes easily accessible in my Dropbox folder on all my computers, in Apple Lossless
4. My iPhone would automatically synchronize my new songs when I am online with my iPhone on the same WiFi network

This seems perfect in theory.  Of course these types of automation seem to usually have problems.  I would need iTunes to automatically remove files from its library that no longer exist (if Media Center trashed the files).

Thoughts everyone?

[WinoOutWest]

Go for it!
I am doing something very similar to my android phones.
I am still manually kicking off the device/folder sync from within JRiver but I like your idea of using the task manger to automate that.
Right now it works quite well.  No more wires to deal with. 
Also I have only set up a one way sync to my phone as I don't really do any "music management" on my phone or tablet.  It also allows me to safely delete songs off my phone that I don't necessarily want deleted from my library.

My components:
1) dedicated directory in a Box.com sync'd folder (I got a 50GB box.com acct for free!)
2) setup dedicated folder as a handheld device and syncing it from JRiver
3) using an app called FolderSync on my various Android devices (phones, tablets) to keep the box.com directory sync'd to a local folder on my device.

It is scheduled to sync daily but I rarely update my JRiver "device" that often - although I am going to look at the task manager and see if I can automate the JRiver sync as well.
Great idea!
Cheers!