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External HDD formatted NTFS keeps my music collection and useful when traveling.

I'd like to keep a synced copy on the NAS as well for use at Home over the network / WiFi

Initiate (manually mostly, maybe automatic) Sync both ways whenever the drive is connected to the network via PC or Laptop.

Ideas?

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Personally I'd use RSync, since I'm a big fan. I assume your NAS is probably already hosting a SSH server, so you should just be able to run. You haven't stated which operating system you're running (Assuming Windows due to the NTFS filesystem, but not 100%), but it should work on all the major ones (Windows (Cygwin), Mac, Linux, BSD)

rsync -Prtu /hdd/music backupUser@NASHostnameOrIP:/raid/array/music
rsync -Prtu backupUser@NASHostnameOrIP:/raid/array/music /hdd/music

You'll have to run RSync twice, once for updating your NAS and once for updating your HDD.

The flags mean:-

-P = --partial --progress
--partial = continue previously interrupted transfers, as oppose to restarting
--progress = print progress to the command line
-t, --times = copy the time metadata to the filesystem (So that the system can determine which file is "newer" on your two-way sync)
--recursive = Synchronise all files, including those in subdirectories.
--update = Do not replace/copy files that are newer on the destination

The combination of using --times and --update on two transfers going in opposite directions means that the end result will be that both origin and destination result in the same file set, those with the newest files.

If you'd like to have automated transfers, the best solution for that would be to utilize private keys for your SSH connection to your NAS, and the scheduling system built into your operating system.

Windows:- PowerShell's WMI Events
Mac OSX:- Launchd's com.apple.device-attach
Linux:- UDev

Etc...

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