Need Advice: Re-Ripping ALL of my CDs using ALAC/Apple Lossless
I need advice from some experienced users (having searched for answers for a couple of days and not finding a comprehensive solution). I want to "upgrade" my iTunes library (95% of which is from my CD collection) from ACC (the default iTunes file format) to ALAC (lossless format). I realize that music purchased from the iTunes store will remain in ACC format, but I am using this opportunity to "archive" or "digitize" my CD collection. I have some, but not a lot, of non-critical tags, album art, etc. set up with my current library. I will be saving all of the music files in a new folder on a single hard disc on my network (with backup). I use iTunes Match. I have Windows PCs, Macbook Pro (OSX), iPhone, iPad, iPod. Given these factors, I am seeking recommendations:
Does it make sense to "start over" and create a brand new iTunes library?
(this would certainly give me time to complete my project while still using my current iTunes library)
If yes, what do I need to do in order to "activate" the new library once it is complete in order to reset iTunes Match and all of the other devices using my iTunes library? What complications can I anticipate?
If no, what is the best way to replace the existing albums in my iTunes library with the new ALAC files? Do I simply insert the CD and import it with my new settings? Will iTunes take care of the rest (saving the new file, deleting the old format, matching tags, etc.)? What complications can I anticipate?
What are the advantages/disadvantages of allowing iTunes to "Keep iTunes Media folder organized" and "Copy files to iTunes Media folder when adding to library?"
Any other suggestions, warning, smart alec remarks?
I know there are a lot of questions bound up in this post, but if you have converted your iTunes music collection to one of the lossless or uncompressed formats, I would love to learn from your experience (and am guessing others will as well). Thanks!
Windows 7