Help with installing new hard drive and transferring data?

I have a MacBook Pro 13-inch mid 2009 that is running OS X version 10.6.8. The hard drive is full and I have a new one I'd like to install, but I am awfly intimidated. I'm hoping that someone could shed some light on kindergarten-style step-by-step instructions on how to make the switch. I'm mostly concerned about the data transfer part. I've found a handy video about physically installing the drive, so I think I'll be ok there.
Here are the items I have in preperation for the switch:
• 1.0 TB Hitachi Travelstar 7200RPM Hard Drive
• Portable bus-powered USB 3.0 storage solution (to turn my old hard drive into an external hard drive)
• Tools including a small phillips screwdriver and some Torx Screwdrivers
• Time Machine Extermal Hard Drive with all of my backups
Here are some things I have read that I find to be confusing
• Some suggest I should transfer my data from the old hard drive to new new one BEFORE I install the new one. (I'm not sure how that works.)
• Some suggest upgrading to the latest OS X before transferring any data. (Would that be Mavericks? I haven't upgraded to that yet. Is that necissary?)
• Some suggest that I will need the MacBook Pro's installation disk to make the switch. (I don't know where that disk is. Do I really need it?)
If anyone can clarify any of the above issues that I've listed as confusing, that would be great. Also, if anyone can help me figure out what steps to do first, second, third, etc., that would be great.
Thanks!

Also,
Will I need the install disks for the Adobe Creative Suite and Microsoft office when I put in the new hard drive?

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