Don't get scared. We have a perfectly good reason for giving The Prince such a high toughness rating. It's not that we wanted to give it a high number, but when we stacked everything on the tough-o-meter, the historical context threw Machiavelli's text off the charts. It's not that the language is hard. Depending on the translation that you're using, Machiavelli's words are pretty simple to understand and his grammar is not too convoluted most of the time. Machiavelli tries his best to be straightforward and the few big words could easily be looked up in a dictionary.
The problem is the context. It's a big problem. So big that nearly every edition of The Prince comes with a huge history lesson, a family tree for the Medici, a glossary, and crazy amounts of footnotes. Machiavelli assumes that whoever is reading his book is going to be intimately familiar with Italian politics, so he doesn't really feel the need to explain everything. We really wish that he did, because the number of names that he just throws out there without context makes it difficult for anyone who isn't an Italian Renaissance scholar to know what's going on.
It's kind of like coming into a movie halfway through, so you have no idea who the characters are. Oh, and it's in a language you don't know. So remember how we said don't get scared? That's because we got your back, and we put together this guide just to help you. Aren't we sweet?