You may want to consider booting off of an exernal firewire drive. I did. No more worries about space.
You could move your home folder to an external drive.
I consider 14gig excessive. A larger size would cut down on fragmentation, I guess.
These utilities will clone your startup drive.
Carbon Copy Cloner will copy your startup drive to an external firewire drive. You can boot from the external drive to verify that you have a good clone. When you upgrade your existing startup drive, you can at any time boot from your external drive and go back to your existing system.
SuperDuper is the wildly acclaimed program that makes recovery painless, because it makes creating a fully bootable backup painless. Its incredibly clear, friendly interface is understandable, easy to use, and SuperDuper's built-in scheduler makes it trivial to back up automatically. And it runs beautifully on both Intel and Power PC Macs!