Originally Posted By: ireckon
Now, assuming that I'm talking about external backup over the Internet, is TrueCrypt a good way to go? To keep it simple and focused, I'd prefer if someone can answer the questions from my previous post.

No, I don't think TrueCrypt or any other local-based encryption/storage method would be the way to go for you. You have stated your requirement for the convenience that is provided by online storage like Carbonite, and I think that is the best solution for you. Other solutions might provide better security and better accessability, but they will require more computer knowledge and will be more inconvenience to use.