The original question had to be edited down. I tend to think that Henry VIII is remembered for two elements. The first would be his desire to move England towards a more secular reality. The establishment of the Church of England as well as himself as its head helped to spearhead the secularization of England. Interestingly enough, one can make the argument that the transferal of wealth and property from English monasteries into Henry VIII's power helped to begin the process in which individuals who depended on the church's benevolence were left to struggle on their own without external help. In a move that will become part of the basis of England's movement to Industrialization, Henry's establishment of a poor underclass is something that will mark the English society as it moved towards a more secular view of reality.
The other element for which Henry VIII will be remembered is with his obsession regarding a male heir. This would mark Henry's "obsession" with regality, something he wore "with a splendid conviction." Henry's obsession with finding an heir and going through wives in vain is something that represents how power, if not controlled, can end up controlling an individual. For Henry, the continuation of regal power held sway over him for so long and in such a magnitude that any primary conceptions about him being a ruler became secondary to the continuation of his rule. While rulers do need to keep an eye to the future, they must also keep an eye to the social maintenance of the temporal condition, something that seemed to move as a secondary issue in the desire to find an heir. In Henry VIII's case, his desire to continue his rule with an heir begged the obvious question whether he had created much over which to rule in the first place.