Comment: Do you need to? (Score 4, Informative) 428
If the current tools you have are getting the job done, I don't see a need to change.
If you want to force yourself into getting started with new technology, I'd start with a rootable Android smartphone, or a Nexus 7 if you don't want to spring for a phone plan. Then just jump right in to exploring it.
You'll learn a lot of the new interface tricks that are shared with tablets/phones, there's a lot of devices and web services they can integrate with, and you can still get your hack on and put SSH and all that other fun stuff on the device.