I think that's what I'll have to do....rename each file and then import them....I guess I fell behind in book keeping.....lol
You should not have to rename anything. My memory is sketchy though. Every picture I owned including some duplicate named pictures were all stored under My Pictures. Some loose, some in subfolders. Then I just imported the whole My Pictures. I think there is a box to uncheck to select importing of suspected duplicates. Initially had that off, but keep it on for new imports. Maybe your pictures that were not imported were suspected as duplicates.
Since my pictures were all under My Pictures, I 'added' them rather than moved. My old folder structure remained. Going forward, I do exactly what Steve mentioned above. New pictures go into a 2014 folder in a sub folder named with the current date. If you moved pictures outside of lightroom, rt click on the folder in the left pane and syncronize again.
I think if you want to start over, you can remove everything from left left pain. Rt click and remove. If you do this on a folder it should confirm that it is removing from Lightroom, but not the actual files. (Maybe just try on one folder before doing the entire collection at once.) So remove folder, re-do the import and choose to import (add) and give the ok for importing suspected duplicates.