Joshua,
I believe I have resolved this issue. Toggling the Limit Ad Tracking on my new iPad ALSO toggled it on my iPhone. I spent the better part of 12 hours trying to debug the same issue on my iPhone running builds of my apps that worked just fine before my iPad. (did this after your suggestion of: Does the issue only happen with your specific device?) Didn’t realize that toggling the Limit Ad tracking switch on my iPad also changed it on my iPhone.
I don’t have an answer as to why/how the hashed device ID never printed out to the iPad in the first place. But I created a new project from scratch, added the SDK & GADRequest, and finally got the device ID to print out for the iPad. (This is after several computer / ipad / iphone restarts, an upgrade to the latest SDK, AND quadruple checking that Limit Ad Tracking was OFF on all my devices).