Playlist membership, ratings and other metadata not stored in tags are preserved during the library relocation and media consolidation process I have given you. Those same pieces of data are lost when you manually remove, move and then reimport media which is why we want iTunes to handle the consolidation.
There are some recent threads covering issues with ESET NOD 32 and Outlook that it might be worth looking at. This search should throw them up for you to review.
Not familiar with iSproggler but any third party tool that attaches to iTunes has the potential to cause problems. Whenever iTunes is updated there is a possibilty that it no longer behaves exactly as expected by the other software. Might be best to remove it if it isn't serving a useful purpose.
iTunes will replace any characters that are not permitted in filenames \ / : * ? " | ; with the underscore character. A leading or trailing space or full stop are also converted. If a folder name or file name plus extension exceeds 40 characters then it is chopped short. If you access the media via an application like iTunes then the exact names of the files and folders really don't matter, but if, for example you have a copy of Friday Night In San Francisco by Al Di Meola, John McLaughlin & Paco De Lucía you'll find that iTunes stores it in a folder called Al Di Meola, John McLaughlin & Paco De L
It is more of an issue with long album and track names. The way iTunes access tracks also means that the entire path must not exceed 255 characters, which is probably behind the iTunes 40 character limit. An extreme example from my library is the Sufjan Stevens track:
The Black Hawk War, or, How to Demolish an Entire Civilization and Still Feel Good About Yourself in the Morning, or, We Apologize for the Inconvenience but You're Going to Have to Leave Now, or, 'I Have Fought the Big Knives and Will Continue to Fight Them Until They Are Off Our Lands!'
which comes in at 288 characters all by itself! My copy (226 chars) is at:
D:\iTunes\iTunes Media\Albums & Tracks\S\Sufjan Stevens\Illinoise\02 The Black Hawk War, or, How To Demolish An Entire Civilization & Still Feel Good About Yourself In The Morning, or, We Apologize For The Inconvenience....mp3
And if I let iTunes rename it then it would end up here for 94 chars:
D:\iTunes\iTunes Media\Music\Sufjan Stevens\Illinoise\02 The Black Hawk War, or, How To De.mp3
If you let iTunes take control (Edit > Preferences > Advance, tick both Keep... and Copy... options, after you've reorganized the library) then you don't need to do anything special. You can rip CDs, download from iTunes, drag and drop files into the iTunes application or the <Media Folder>\Automatically Add to iTunes folder, or use the File > Add Folder to Library menu. iTunes will take care of moving things to where they are supposed to be.
tt2