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iTunes is a piece of shit.

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No, it wouldn't, but I'm willing to bet the people who want or need folder monitoring are in the minority. (From my experience) the majority of people who use iTunes download an album, drag it into iTunes and are done with it. Your way is downloading an album, dragging it into a folder and being done with it. Same number of steps, but a different way of doing it. So I don't see folder monitoring as being some huge missing thing that iTunes needs to have.
Set the bar low.
 
Weird. I've been using iTunes for years on my Mac. It's never been too bad. Runs pretty well on my PC now too. I have no major issues with it. I do wish that someone would make a worthy competitor though. Everything else kind of sucks
 
No, it wouldn't, but I'm willing to bet the people who want or need folder monitoring are in the minority. (From my experience) the majority of people who use iTunes download an album, drag it into iTunes and are done with it. Your way is downloading an album, dragging it into a folder and being done with it. Same number of steps, but a different way of doing it. So I don't see folder monitoring as being some huge missing thing that iTunes needs to have.
Actually there is a folder called "automatically add to iTunes" to where you can drag your shit and it will show up on iTunes.

Most problems with the software are simply related to not knowing how to do something on it or having a crappy computer/OS setup.
 
Okay, so instead of sorting through 60 gigs of music that iTunes randomly threw into the recycle bin, I just put all of it back into my "Automatically Add to iTunes" folder. Now there's gonna be a fuckload of dual entries for all these items. One for the "new" files that I just added, and one entry still looking for the old files. I'm hoping to not have to troll through my entire collection and delete dual entries and I can think of two solutions, depending on how iTunes does things:

1) Is there a way to automatically delete all entries with missing links (entries with the red exclamation point next to it). All of the files that got deleted have red exclamation points on them now due to the metadata trick someone shared with me earlier in the thread.

2) I could just have iTunes rescan and create an entire new library. This is gonna take like 15 hours though and will my playlists/other things be fucked? What happens when I plug my iPod back into the computer?
 
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