Got new Nano. Now only a small part of library will sync.

I upgraded from a first gen. 4gb Nano to a brand new 16gb Nano. I had about 3gb in my old nano and added songs frequently with no problems. I tried to sync my new Nano tonight and only about 500mb would sync. Now I have exclamation marks next to 75% of my library. I added some new stuff to see if it would sync, and it did. I just can't sync the old stuff. Help!

Again many thanks. I have tried to tidy up the folders as per your idiot guide- which term is appropriate for me
Under iTunes Media though I do not have  folders for Books,iPod Games, Mobile Applications, Movies, TV Shows so I only have  Auto Add to iTunes, Music, Downloads and Podcasts - My question here is is this OK.
Next - Library files that you mention are there but do not end .itdb
Next  - in the main iTunes folder followingon from Artwork and Media folders  there is some other  iTunes database stuff like Library Extras, Library Genius, Library and Music Library(xml) all dated 10/02/12 plus MimiPlayer .dll dated 21/02/14 and Set Up Short Cut dated22/03/14  
AND there is also a Programme Files folder with a sub folder holding file folders called CD Configuration,iTunes Resources, iTunes Help Resources, iTunes Mini Player Resources and Mozilla Plugins all dated 24/03/14 ( when I downloaded the new iTunes) and then a lot of application extension stuff from 2011
To recap I unistalled the old 32 bit iTunes and installed the new 11.1.5 (64 bit) version over the weekend  SO is any of the old stuff listed above required.
Outcome right now is that as previously I can only call up the Downloaded music not Podcats or CD copies.
Regards
David Pugh

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