Over the last two years I've had the opportunity to work with him and his staff. Some personal observations:
1. No, he didn't understand technology. He understood marketing. Indeed there where times when he would remind me of Frank Abagnale Jr impersonating a doctor or lawyer. When the discussion would turn technical he would get this deer-in-the-headlights expression. Perhaps most troubling was his lack of even a basic understanding of IT security concepts; as the Federal CIO you would have at least expected someone who would try to understand the legal obligations involved.
2. He couldn't take criticism. When government reps raised security issues with his cloud plan, he would turn to his industry reps who would reassure him everything would be OK. He surrounded himself with yes-men, creating an echo chamber where anything that would contradict his 'brilliant' ideas would be promptly excised.
3. Outside OMB, he had no support in the federal government. Federal CIOs treated him respectfully, but they knew he had no legal or fiscal authority for any of his plans; most decided to play along and wait for his term to expire. His relationship with Congress was even worst; the Hill would usually outright ignore him.
I already know of several Federal CIOs who are now revising thier 2012 budgets to write out Kundra's pet programs. His legacy would go past this October.