I've never used Lightroom but I love Aperture for it's photo management. It really streamlines the entire process you're talking about.
You've got to let go of managing your photos in the way you have. I can't imagine using the finder for any sort of photo management - you can't see any of your metadata! How is that even remotely satisfactory?
Install Aperture and update it to 1.5.3. Use it to store references to your photos and give it a try. After a while, you may let go of the need to manage your files' locations and just use the library to do it for you. I have and it greatly simplifies everything. However, offline files are fantastic since you can span your photos over multiple volumes and manipulate the meta data with ease.
Use either Aperture or Lightroom. There will be a learning curve but it'll be worth it.
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