Oops...pre-install advice, please...

My OS partition on the MBP is about 5G shy of being full. When I got this machine last December, I figured 40G was enough; never thought that Apple OS would be so bloated and big. Well, it is, and I'd like to bump up to Leopard sometime soon, but find myself in a quandary with the amount of space left. I'm sure Leopard won't fit on what I've got left.
SO...what are my options? Is it possible to repartition during the upgrade and spare myself a headache, or am I just hosed? Or is there something wrong with my OS and there's a bunch of hidden stuff I can get rid of? Or...?

Your system looks all absolutely normal. Yes, don't repartition next time - there's no need whatsoever, and it always leads to all sorts of problems exactly like this.
To clone your system disk, it's easy, but read through this first (and other online options if you like - search for 'cloning bootable backup') to reassure yourself you're ready for it, as you will be erasing everything on your disk to do this, so it's not for the faint of heart.
Hook up an external firewire disk and ensure it's formatted as HFS+(Journaled), open Disk Utility, click on your system partition, go to the Restore tab, drag your system disk to the Source field and the Firewire disk to the Destination field, and click Restore. Once the copy to the external disk is complete, select that Firewire disk as your Startup Disk (in System Prefs) and reboot to confirm it all works OK. Your computer will restart from the external drive and should to all intents and purposes appear to be completely normal except a bit slower. Now you can copy all the contents of your 'Media partition' over to the Firewire drive too - put it into a folder in your home folder.
Note that you can also use third-party drive cloners like SuperDuper or CarbonCopyClone to clone your system partition. All options work well, but Disk Utility doesn't cost you anything.
Now, once you're absolutely sure all is working fine from your external cloned drive (maybe run a few apps, browse your iTunes, etc), you can repartition to 1 partition and erase your original laptop drive. This will DESTROY EVERYTHING on that drive, so proceed with caution.
Once that's done, you can use Disk Utility to Restore in the opposite direction as before - using the Source as your Firewire disk and the Destination as your laptop disk. Then reset your Startup Disk to be the laptop drive and now you should have a laptop with a single partition and everything on there. As a side benefit, you now also have a bootable clone of your system disk on the Firewire drive!

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