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If you are going to do lots of re-organizing, I would create the folders on the desktop (i.e. outside of LR), but move the files in LR. This way LR will know where the files are now located as you move them.
If you do everything in the Lightroom Folder panel, You can create new folders and a new folder structure in the folder panel then drag images from their existing folders to the new folders. Or who folders of images to a new parent folder. Since this is a Lightroom operation, Lightroom will automatically update the path stored in the catalog file when it moves the image files or folders. That way you do not need to have a nightmare of relinking manually.
Thanks for all the help everyone. One more question - when I upload photos from my memory card to my laptop, they go into a Lightroom folder with that day's date under the parent folder for the laptop hard drive (MacIntosh HD). My plan was to build folders on the Lightroom panel in the external drive parent folder (My Passport for Mac) that correspond to the Collection folders, where I put my photos after I've imported and sorted. Then I was going to add the photos from the individual Collection folders to the corresponding external drive folder. IS that too much manipulation? Should I just have a folder on my external drive for each year and throw the whole imported date folder in there every time I import? (Also, I'm assuming when I'm moving photos out of the dated folders in the Lightroom panel I can just delete those folders that end up having "0" photos in them?). My brain is fried!
What are you going to do when a photo is in two collections? For file management purposes, my preference is to use a date-based folder system and then use LR to create collections (and/or use keywording). There are other methods that folks use, but I prefer date-based folders and names. No file has the same name, and if I need to do backups, I find that this arrangement is easier for me. And if I send somebody a file, I can easily locate it years later if it has a date-based name and I have a date-based folder structure. I acknowledge this is not everybody's cup of logic and arrangement, but variations on it are quite common among forum members. YYMV.
