The Prince is a quick read, and because I'd read chunks of it in high school, I mainly just got impressions of Machiavelli. First off, he's whiny. Complains about his situation, and flatters Vettori enough that his section warning of flatterers comes off pretty silly sounding.
As I read through his various judgments and recommendations I had to stop myself from thinking this was a mordern-day U.S. conservative manifesto. Damn the collateral damage, don't take private property, and if you need to bust some heads to achieve your goals, bust away. That's not entirely fair, and I won't make the proclamation that conservatives are Machiavellian. It's more that it seems to come easier to them. Liberals have all sorts of moral compunctions about this sort of thing, and often it doesn't serve us well. Perhaps in the back-and-forth, rhetorical battles, liberals should fight a bit more like Niccolo Machiavelli.
Interesting read for that perspective, the sometimes-thoughtful argument, and to understand the reason he became an adjective.