There's no tutorial for your special circumstances:
+After I have upgraded to newer versions of iTunes in the past, I always have lost tons of music, although most was recovered either by reripping CDs or by scouring my harddrives to locate the original files+
This isn't supposed to happen. An upgrade shouldn't be 'losing' anything. It should update C:/Program Files, put an old copy of the ITL in the Previous iTunes Library folder, and not touch any of your music/video/podcast etc files.
To get to the root cause - what do you mean by 'losing' tons of music?
Are you getting the dreaded ! original file not found message?
Are you storing your media on external hard drives? Do those drive letters always stay the same, or do they change depending on what you have plugged into your USB ports?
Here is the best explanation I've seen of itunes library database vs itunes library content. Some folks say it's too wordy, but the paragraph of databse vs content is very informative.
http://www.ilounge.com/index.php/articles/comments/moving-your-itunes-library-to -a-new-hard-drive/