Ah Florence. There’s nothing quite like complete and utter military incompetence due to governmental in-fighting and a lack of money due to an overpowering fear of taxation. Though Soderini did his best to rey and resolve the issue when he was gonfalonier (1502 to 1512) but then the Medicis came back and it all went to hell in a very fast, expensive, bright red car. Or something to that extent.
Machiavelli can tell you more. Though it will read rather jaundiced and jaded. Though having been tortured by the Medicis, it’s none too surprising his lack of enthusiasm for princes. (contrary to popular belief).
Charming!