Hi everyone, I've been trawling the forum looking for answers but I would like to get some specific help and other users experiences of iTunes PC to Mac migration options. I have been a PC user since I got my first PC about 15 years ago. About a year after I bought my last PC (an Dell Inspiron) I decided I'd had enough and next time I was upgrading I would get an iMac. The Dell has started to act up and I am able to order discounted computer products through an Apple reseller so I have ordered a 27" iMac to be delivered in early January. I want to migrate my iTunes library accross to the Mac. I have had the same iTunes library since iTunes was first released on the PC and I let iTunes keep my music folder organised. I am anal about my music collection so everything as I have collected it is also stored seperately on an external drive in a very meticulous way often with lossless versions of stuff I have ripped myself as well. I don't ever listen to this as it's mainly just as a backup. What I can see is I have three options: 1. Transfer my library over. I have seen tutorials of how to do this and I have transfered it from PC to PC before so I reckon it'd be handy enough. Only thing is my iTunes library is messy and I wouldn't mind starting from scratch again. 2. Create a new iTunes library and just drag the stuff I want in it from my external backup drive into the iTunes library on the Mac. But if I do this will this mess up my iPhone syncing? 3. Sign up to iTunes match. I was thinking of doing this anyway and I was wondering if anyone has used this to transfer a library from PC to mac? I like the idea of upgrading my songs as I go but I have a load of rubbish compilations in iTunes belonging to my wife (who now has her own computer and I don't really need.) So wondering if cleaning up iTunes with a new library before I go is the way forward? I also use an iPhone but this is backed up through iCloud so contacts, calenders, etc will just sync through that. It's only really the music aspect of it I'm concerned about. Any other users give me there opinions on which is the best and quickest option for me? Anyone else migrated over and what were the experiences? Any problems encountered? Thanks in advance.