Given that there is probably nothing wrong with Ireland that isn't some way Henry VIII's fault (except the weather) then it shouldn't be surprising which way he voted.
But to compare him to Stalin and Hitler (Or to compare any medieval or Rennaisance monarch to the autocrats of the age of the dictators) is a false comparsion and completely misunderstands the nature of kingship and monarchy in that period.
EDIT: But this forgets Elizabeth I > Henry VIII.
Yes, but he was too a great ruler
Not at all. England was not in great shape in the years following his death.
In what way? I'm not saying i think Henry was a particularly good king - in some ways he was quite a weak king, heavily influenced by those around him - but i'm intrigued as to what precisely you're referring to; the so-called 'mid-Tudor crisis' has long been out of fashion among historians of the era (that's not to say there weren't problems, just that the association of them with the regimes is not necessarily apt).