Recently I've started working with Rand on doing site analyses for our clients. He's taken me under his wing by walking me through a typical site analysis and telling me what to look for. Obviously, since Rand is the resident expert, it is easy for him to know what to look for and what to recommend to the client.

Unfortunately, up until I started working for SEOmoz, I was accustomed to surfing into a site and taking it at face value. I now have to train my eyes to see things as an SEO expert would. How do I train myself to do that? I'm currently taking the hands-on, shadowing approach with Rand, but I recently read an interview with Michael Gray (aka Graywolf) on the Sootledir Marketing Blog that offered another site analysis tactic:
When I was first starting out I’d do it with index cards writing down all of the onsite factors for site1.com on one index card. Then I would do the same for site2.com and site3.com. Do the same for links. Then take all the links cards and spread them out on the table looking for commonalities in linking patterns.
In terms of visual, hands-on exercises, his advice is pretty sound. It's a good way to get assimilated and accustomed to comparing and contrasting different sites and training yourself to catch site weaknesses.

Do any of you have additional advice to offer an untrained eye? What's an innovative, clever, or simply tried-and-true way to train yourself to know what to look for when analyzing a site (other than the typical get-better-the-more-you-do-it approach)?