Clean install without losing everything

I need to upgrade to Tiger in order to run MSOffice2008.
I've been told by several people that stepping up to a new OS generally goes better with a 'clean install' which I understand to mean completely wiping out my hard drive -- starting over from scratch basically.
So I'm trying to figure out how to do this without losing all my stuff.
My plan/My questions
1.) Back up everything to an external hard drive (Any suggestions for a good 250-500GB drive? Is there any software that can be used to 'manage' this kind of back up?)
2.) Format the drive. (How exactly do I do this?)
3.) Bring all my documents and apps back. (The documents are easy enough to bring back, but I'm worried about the applications. For example how do I get all my emails back for the Mail app? What about my different Quicken records? Aren't applications kind of split into pieces and spread over different locations (like librarys and stuff?). If so, how do I get them back? I can reinstall them (like Quicken) from their disks, but how to I get my data?)
Hoping someone can point me in the right direction to get started.
Peter

Any suggestions for a good 250-500GB drive?
250GB...
http://eshop.macsales.com/Item_XLR8YourMac.cfm?ID=6383&Item=OWCNPFW7250GB
500GB...
http://eshop.macsales.com/Item_XLR8YourMac.cfm?ID=8750&Item=NWTMS2F7500G16
Format the drive. (How exactly do I do this?
Actually, on the two I linked to, they are already formatted for Macs & pretested, but should you ever need to, or just want to partition it...
Either open Disk Utility in Applications/Utilities from your Hard Drive, or...
" 1. Insert the Mac OS X Install disc that came with your computer, then restart the computer while holding the C key.
2. When your computer finishes starting up from the disc, choose Disk Utility from the Installer menu. (In Mac OS X 10.4 or later, you must select your language first.)
Important: Do not click Continue in the first screen of the Installer. If you do, you must restart from the disc again to access Disk Utility."
Highlight the new drive, select erase, and btw, check install OS9 Driveers if you think you might ever need to read or write to the OSX volume from OS9.

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