I don't have the skooba exactly, but something similar. In NY (JFK) they made me take out the laptop (and I also by the way am a member of the Global Online Enrollment System and have been vetted so I shouldn't have to do it anyway). In north dakota and st louis it was fine. Just as an example.

Personally, I spent a lot on money on a macbook pro, so I would rather have it more protected than save the few minutes with the TSA. There rate-limiting step is usually the line and not taking my laptop out and putting it back anyway.