Its easy to judge history now but that's not the correct way to see things. You need to see things from his perspective. Tudor took a stable and respectable kingdom to the brink of civil war and invasion. Smallfolk were left dying on both sides (first Catholics, then Protestants under Mary, then Catholics again) and his dynasty ended after 1 generation. His crown ended up first to Mary, the very daughter of the woman he turned against then to Elizabeth the daughter of the woman he executed.
Regarding monasteries, I agree wholeheartedly and I assure you no one understand the injustice of a rich church in a poor country then I do. This situation survived in Malta well past medieval times, as the church and the British empire agreed not to step at each other toes. It was only after independence when Mintoff finally put the church in place and it was a fight him and his supporters (including my grandfather) had to fight for inch by inch and suffer a horde of injustices because of it. Yet, you also need to understand the times too. During the medieval times, that wealth could end up either to the church whom, with all its weaknesses, did care for the poor else it would end up in the hands of nobility who didn't share any love for the poor.