Help a noob create a semi-complicated sync recipe.

I would like to use Hazel in the situation described below. I can also use Automator, Applescript, or any other program necessary, but my knowledge of these programs is as basic as it can be, so if you can help me, please try to take me through things step-by-step.

Background info:

I have a folder on my Desktop called “TV.” “TV” contains subfolders “The Simpsons,” “Orphan Black,” and “Sleepy Hollow.” When I acquire a new episode of each show, I place it in its folder under the name “Show Title S**E**.”

“TV” also contains a folder called “Watched.” “Watched” contains subfolders “The Simpsons,” “Orphan Black,” and “Sleepy Hollow.” When I have finished an episode of, say, Sleepy Hollow, I move it from Desktop > TV > Sleepy Hollow to Desktop > TV > Watched > Sleepy Hollow.

This is what I want Hazel to do for me:

When I connect my portable HD, I want the files in Desktop > TV > Watched to be moved (not copied) to a folder (also called “Watched”) on the portable HD, with subfolders automatically created for each show. I want the folder structure in Desktop > TV > Watched to be preserved, so that I still have the folders “The Simpsons,” “Orphan Black,” and “Sleepy Hollow,” but the video files are now on the portable HD.

Connecting the portable HD does not have to be the trigger for the rule(s), but it would be nice.

Can anyone tell me how to do this?

If anything needs clarification please let me know.

Cheers.

No need to think about "triggers" in this case. Just create the rule with the drive connected. It will fail when the drive is not connected but will try again when it is connected.

To do the copy, there are multiple ways of doing this but first off, check the sticky article about going into subfolders. You'll need that to tell Hazel to go into subfolders to operate on the files within. From there, have another rule to do the copy. There's an option in the copy action to copy over the file structure as well. Tweak that to your desired structure.