Okay, I found a new website tool that has a lot of potential. It is called “Be IMBA!” (catchy name!). You can enter a (level 70) character’s name and realm and the website will suggest how to improve the character for raiding (gems, enchants, talents, and gear to an extent). It will also assess the current state of the character and make a guess as to what level of raiding the character is ready for (Kara, T5, etc.).
You can also plug in a server and guild name to have it run a report for an entire guild’s level 70 characters all at once.
Obviously, this has a lot of potential for misuse at the moment. Off-specs whose itemization is sometimes a bit wonky *cough*shadowpriests*cough* are penalized in ratings (as it seems to be based off of iLevel). It also makes unnecessary suggestions, or tells you to improve things that really don’t need improvement. However, this website is very new, so kinks are still being worked out.
This site does make me a little sad on the inside. Why worry about understanding game mechanics when you can just plug your character into a website and have it tell you what to spec, how to gem, etc.? Hopefully people will see this as suggestions and not gospel (and hopefully raid leaders use good judgment when using this tool to assess their guilds).