How would Machiavelli critique our contemporary society? What things might he condemn, and what might he praise? What might he recommend as worthwhile behavior? In addition, to what extent do you see his ideas exemplified in our current society? Do you think society could be improved by implementing more or few of these ideas? how so?
Well, in regards to your first question, it's important to understand that Machiavelli is NOT talking about democratic rulers, he is talking about autocratic rulers; therefore, not all of the advice in The Prince would apply to our world today.
In looking at countries like China, however, perhaps they could learn to allow their citizens more freedom in order to inspire love for the government instead of less freedom in order to inspire only fear. This could be one instance when Machiavelli "critiques" our contemporary society (or, at least, that of China). Machiavelli believes, of course, that both fear AND love are needed for the most pragmatic of rulers. That is hidden between the lines of this statement:
It is better to be feared than loved, if you cannot be both.
In regards to democracy, even though it isn't dealt with in The Prince, Machiavelli does believe that leaders need to change both their tactics and their ideas when needed. Machiavelli insists that even the best-made plans of any ruler might need to be put aside for the betterment of the country and its people. Machiavelli would certainly recommend this as good behavior for any ruler or democratic governing body.
Here, I must talk a bit about Machiavelli praising good male role models. This is one idea that I think we could get behind.
A return to first principles in a republic is sometimes caused by the simple virtues of one man. His good example has such an influence that the good men strive to imitate him, and the wicked are ashamed to lead a life so contrary to his example.
So, perhaps we can take this as both a recommendation in our modern society, an example of "worthwhile behavior," and how ideas can be "exemplified." Good male role models are always needed.
In regards to "society being improved by implementing more" of these ideas, in general I disagree. Look no further than our own English language and the word "Machiavellian." The definition of Machiavellian is
Being or acting in accordance with the principles of government analyzed in ... The Prince, in which political expediency is placed above morality and the use of craft and deceit to maintain the authority and carry out the policies of a ruler is described.
Note that "political expediency" is more important than "morality." Deceit is also used for crafty and secret and even dishonest plans. In fact, the difference between right and wrong isn't even important; therefore, all that matters is that a ruler keeps his/her rule. In my opinion, morality should never be put under the foot of politics.
The irony here is that this "new" word and definition IS how Machiavelli's ideas are "exemplified in modern society." Unfortunately, it's not the legacy for which he hoped.