During upgrade, will it keep all apps?

If I upgrade to Leopard do I need to reinstall all my applications including Parallels? I currently have Max OS X version 10.4.11.

You can boot from the external drive and make sure it's working well, then insert the Leopard DVD and launch the installer. It will tell you to restart your Mac and boot from the DVD. Run the installer and it should show you two drives that you pick from to Upgrade.
Or
Boot from the Install DVD and tell it to install Leopard. The installer will list both drives, and since there is the same Tiger installation on both drives you will be offered a choice of which drive to install to. Then the options for the type of installation are available, and choose to upgrade the drive.
Or
You can even insert the DVD, and when it is mounted, go to System Preferences/Startup Disk/ and choose the DVD and click on the restart button.
Use whatever method you feel most comfortable with, they all work the same. Leopard has to install from a booted DVD.
After the installation you repair your permissions by using Disk Utility then run the OS 10.5.7 Combo update you could have already downloaded from here:
http://www.apple.com/downloads/macosx/apple/macosx_updates/macosx1057comboupdate .html
Then run Software Update to get the latest versions and bug fixes for your Apple Programs. I'd run all of the updates before using any of your programs.
Meanwhile, your original working copy of Tiger can be booted back into, if Leopard hits the fan...

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