Presently I am still enjoying the honeymoon phase of my new laptop. To avoid the slightest appearance of ostentation, I will refrain from going into details of exactly what laptop I got, except to say that it is of course a Mac, and it's REALLY REALLY cool!
Apple provides a Migration Assistant that apparently will copy all of your files and settings from your old computer, so that your new Mac looks exactly like your old one. My feeling about this is: Why would anyone want that? For me, one of the pleasures of a new computer is that it's *clean*, unburdened with hundreds of files scattered around my home directory that I never use but are too important (or too numerous) to simply delete.
So for years, whenever I get a new computer, I never copy my files over en masse. Instead, I copy over a small set of files that I know I need, and leave the rest on a backup. Then the next day, I find that I need a file on the backup that I didn't realize, go back and copy this over, etc.
This process stabilizes after a week or so, and my electronic life feels much less cluttered.
I suppose that I could just blow away my home directory every year for the same feeling, but somehow it is hard to convince myself to do this.
I wish that I could use the same process for physical papers, but sadly paper information cannot be stored as compactly as its electronic equivalent.
Super-Mac-Geek-Alert: For several years, I have been using Keychain to store secure notes such as password hints for bank logins, etc. I thought I was very clever to avoid impressive but costly tools like 1Password. Then I tried to copy the Keychain to my new computer. Painful. I think from now on I'll keep these notes on a small encrypted disk image.