I'm having some challenges setting up my new Macbook Pro (first time Mac owner) with iTunes, my external hard drive, and my NAS device. Any help is much appreciated. Background: On my PC laptop, I had my iTunes folder (no music, just the .itl file, etc.) stored internally and had the iTunes media folder location directed to my external hard drive. As long as I had the external hard drive plugged in before opening iTunes, it would find the music just fine and keep the external as the "go to" place for the media folder location. No problems. Then I got a D-Link NAS and I was able to set that up with no problems (surprisingly) and I would keep that as my iTunes media folder location and still keep my iTunes folder with no music, just the .itl file, etc. stored internally on the hard drive. If I ever had to travel/leave the house with my laptop, I would just bring the external hard drive with me and reset it as the destination for the iTunes media folder location. No problems. Then iTunes 11 came along. In hindsight I'm not sure if it's iTunes 11 or my crappy D-Link NAS, but it took about an hour for me to reset the iTunes media folder location and even longer for me to "keep iTunes media folder organized" (upwards of 2 hours). I've now bought a new Macbook Pro and my Synology NAS will be here Tuesday. In the meantime, I copied my iTunes folder (with the .itl and other such files--no music) from the PC to the new Mac in order to keep all of my album art work and playlists. They all show up fine in the iTunes program when I open it. I'm wondering if it's normal with iTunes 11 to have such slow times to set the destination folder for my music and to "keep iTunes media folder organized"? Was the D-Link NAS the cause of being so slow? I am trying to do this with my external hard drive and it's taken literally half of the day to "organize" all of the files, even though they were already organized just fine on the PC. The first time that I tried this, after about 6 hours of organizing, a window suddenly popped up and said that it could not locate the NAS device. I'm not using a NAS yet--just the external hard drive. Needless to say, this was super frustrating as I have to restart w/the location and the "keep folder organized." Surprisingly the location only took about 20 seconds to set the 2nd time (took about 2 hours this morning). Now I'm waiting hours again as it processes "keeps folders organized." I'm wondering if there's something in the iTunes folder on my internal hard drive that still wants to locate the NAS device even though I have none hooked up. So, with all of this time on my hands to think about this as I'm waiting for the files to organize, I'm wondering a couple of things--I hope someone knows this or has tried this!: What I'd like to do is, after this is done, set up Time Machine (which I am NOT familiar with) to remember my setting with iTunes and the external hard drive (assuming it will complete the "keep files organized" this time). THEN when I get the NAS, I will set up another Time Machine stamp to remember the configuration with iTunes, the destination file as the NAS/music folder, and "keep files organized." I'm wondering if, when I travel, I can go back to my time when the external hard drive was hooked up to iTunes and I won't have to go through all of the "reorganizing" again. And then when I return, I can revert Time Machine back to my latest time using the NAS w/iTunes. Also, what will happen if I add new files to either? I just need to create a new Time Machine stamp? Anyone ever tried this? Also, if anyone has input on why it's taking so many hours to find the destination music folder and "keep music organized", that would be very helpful! Sorry for the long write-up--I wanted to be as detailed as possible so as to figure out a good solution to this problem! Thanks for all of your help and time!