How do I consolidate data following several failed updates?

(Not a Mac newbie, but as green as one....)
Last week I tried to upgrade to Leopard and then onto Snow Leopard, but each has failed and stalled. I've now gone back to Tiger, but where I was testing each upgrade and slowly pulling my backed up data over, I have now got several tonnes of backed up data but I'm not sure which one is which!!!! I know that I've made a pig's ear out of it but can anyone suggest a piece of software or a method to help me wade through everything and delete the duplicate files???
I'm now staying firmly put on Tiger until I'm able to figure out why my laptop kept crashing....Its really not nice having the spinning wheel of doom or the prohibitory screen greeting you every morning :o(
Any advice greatly appreciated!

Whew... I think we should start with figuring out or eliminate any possible reasons for the crashing.
Boot off your Install Disk while holding down the *d key*, (not c key), then run the extended Apple Hardware Test. Some disks require you to use the Option key at bootup to select AHT. Some models have a separate AHT CD.
"Try Disk Utility
1. Insert the Mac OS X Tiger 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.*
3. Click the First Aid tab.
4. Select your Mac OS X volume.
5. Click Repair. Disk Utility checks and repairs the disk."
http://docs.info.apple.com/article.html?artnum=106214
Then try a Safe Boot, (holding Shift key down at bootup), run Disk Utility in Applications>Utilities, then highlight your drive, click on Repair Permissions, reboot when it completes.
(Safe boot may stay on the gray radian for a long time, let it go, it's trying to repair the Hard Drive.)
The usual reason why updates fail or mess things up, is if Permissions are not fixed before & after every update, with a reboot... you may get a partial update when the installer finds it doesn't have Permissions to change one obscure little part of the OS, leaving you with a mix of OS versions.
Some people get away without Repairing Permissions for years, some for only days.
If Permissions are wrong before applying an update, you could get mixed OS versions, if Directory is the slightest messed up, who knows!
If many Permission are repaired, or any Directory errors are found, you may need to re-apply some the latest/biggest updates.
May even need to do an Archive and Install if you have room on the HD, but saves all your files and gives a new OS...
http://docs.info.apple.com/article.html?artnum=107120
I only use Software Update to see what is needed, then get them for real via...
http://www.apple.com/support/downloads/
That way I can wait a week or so, check the forums for potential problems, and get Permissions & such in order before installing.
On duplicate files it's a tough decision, but the two methods I use are...
Drive Genius 2 & it's Drive Slim function…
http://www.prosofteng.com/products/drive_genius.php
Or my favorite, Tri-Backup...
http://www.tri-edre.com/english/tribackup.html
It can be set up to copy Disks or Folders & choose options like replace newer files or not, it also has a neat compare folders/drives & show you the differences & if files are identical or not.

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