I had a similiar problem when I first started using calibre. I had about 7 gig of files I was trying to import at once. Someone suggested (Starsun if I remembercorrectly) that calibre had more trouble with certain file types. pdf and html perhaps, not totally sure.So I did a search for each format and cut and pasted them into seperate directories. Pdf, epub,lit, mobi, zip,rar, htm etc.
Then I imported one directory at a time and it went perfectly.
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Before you fly off and bulk convert (if you need to). take time and get your default conversion settings refined to your liking.
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This is totally good advice and will save you a lot of grief.
under preferences->adding books:
Two preferences that make a difference in importing time I have been told is to have automerge turned on and to have read metadata from file contents turned off.
Before beginning again, I would suggest looking at your authorsand see if the majority are in the right order. Then decide whether to have swap firstname/last name.
Recently, due to a corrupted database, I re-imported my entire library and it took under 3hours for 18+ gig of files. of course these files had already been processed.