I know I've seen the argument before that The Prince is actually a subtle satire--or maybe backdoor proponent is a better phrase--in favor of democracy based, as you point out, on Machiavelli's own service in a (more) democratic government, but it's certainly not the common interpretation.

Then again, I often think that if "A Modest Proposal" had been published today, there'd be a contingent online sincerely in favor of baby-eating based on it.