Do you have a checklist or drill for getting on board with a new computer?

When you have to move into a new computer, do you have a standard routine for getting everything transferred over or reinstalled? I fear and dread the prospect almost as much as I fear and dread having the current laptop fail on me.

Is there a Best Way to approach this? My current laptop is four years old, so I’ll probably be in that position sooner rather than later, and my husband is no longer here to coach me and hold my hand.

 
This question is piggybacking on @jca2’s question here.