Hamilton was the beginning of all that is bad in the Federal government.  He was a smart man (unlike most of our politicians today), but he also had very tyrannical tendencies.  Still, I think he would be appalled with what we have become today (culturally and what our government has become).  As bad as he was, I don't think he would like what we have today. 

 I think you're right. Hamilton probably would be proud that America became a great and powerful empire and that the president is more powerful than the monarch of Great Britain, but he surely would be appalled at what the USA has degenerated to.