I do not know about iTunes library.
I believe that the essential element in database management is to try to create unique file folders. On my music drive I keep 3 primary music folders. Rock (my largest collection), Jazz (next largest) and Music (with sub folders like country, classical, new age etc.). I have over 3,000 artists and over 3,000 Albums and keeping this straight is essential for me. When you have a small number of files it is less important to develop a good structure. All this adds a little work but it is very helpful when I am working with my folders in windows. Because there are so many groups with "The" in front of their name I change it to "Rolling Stones, The". If I didn't then the majority of my folders would be under "T". I also reverse names "Adams, Bryan". Again this helps to keep files folder unique and easy to find. When I Rip a disc I use the secure mode and I still favor "EAC" because of the accurate rip feature they offer. MC has a very good ripper and is certainly on par with EAC. However, I want to know if one or more of the tracks I rip is less than 100% accurate. If they are not accurate then I mark the file with (def) in the song title. This way I can replace the file at a later date if and when I can get a clean copy of the that song.
I do not have a separate file folder for various artists. I rip them the same way I do albums and create a file folder for each artist\album\song title. I don't add the track number to the song title as MC tracks all that info and is created in the tag unless it is a WAV file. Again, this keeps all the tracks associated with a given artist in the same folder (Artist). When I tried using other methods I had a difficult time with album art. Some of this has been addressed with MC's ability to look up album art. I used to keep various artist in a separate folder but as my collection grew it became a problem to maintain. I also strive to make sure that all my song titles have each word capitalized. There are some great edit capabilities within MC that I use all the time.
Under tools\library tools\clean file properties: You can select which fields you want to operate on like Album, Artist. Artist (Auto), Album Artist, filename (name). These are the ones I use all the time. I can convert underscores to spaces, remove leading and trailing blanks, change spacing to single space, move articles to the end (I don't use this since I do it when I rip) and Fix capitalization Upper Case All Words. When I import new music this is one of the first things that I run. This is a great way to make all your files standardized. If you are operating on a single file you can always use the Tag editor to make the changes you want.
You can also use this feature to change the names of the actual files (filename (path)). Beware that this could cause some problems as this may create new folders and it will move the files to the new folder but it does not move album art if you store it in the file folder with the songs (I do). So in that case you need to move the album art and delete the original file folder. I don't use this tool very often, I prefer find and replace when I deal with the path filename.
Sometimes I have a problem with the tags as written by EAC. In that case I can use (under library tools) fill properties from file name. It will populate artist, album, and song title. If you have a various artist folder this becomes very messy.
I have been adding a lot of CD's this past year and I am approaching 40,000 tracks. I store everything lossless Flac because there is more and more hardware that will play flac files. APE is a superior compression program. Either one is an excellent choice for lossless format.
There are many others who can help you with syncing to your iPod or other portable devices.
The tag editor is a very useful (under action window Tag) tool. Under Filename you can edit the filepath song title and it will rename the song title (and it stays in the same file folder).
There are so many options to use in MC to maintain your music files. In my opinion, it is the best database by far and I haven't found a better player.
Tunetyme