There's an alternate reading of The Prince as a pro-democratic piece - throughout the entire work, Machiavelli reminds the titular Prince that the strongest cities, in terms of power, were those that were governed democratically, where all men of the city felt that they were defending, not just a prince, but an institution they were a part of. Almost all of his infamous pieces of advice are prefaced with "this is the second best answer, and only if you absolutely must hold on to as much personal power as you can."
This is my preferred reading as well - the dude is pro-democracy _specifically because_ he knows what the right move is for a king, and it sucks for everyone else.
He wrote the book as much as a warning as as a reason for the prince to invite him back to Florence.
EDIT: grammar, is -> are