Regarding upgrading the hard drive, you can use Time Machine in OSX to make an image of the drive. After you switch out the drive in the Mac, you can boot up from the OSX disk and tell it to restore the last Time Machine archive instead of doing a clean install. I apologize as I can't recall the exact steps, but I did this on my Wife's MacBook Pro when the original hard drive died...so it is doable. :)
The down-side is that you have to have a Time Machine disk to backup to. IIRC, not just any drive will work either - it needs to be a "Time Machine certified" drive or something along those lines.
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