AHC: Mediaeval/Renaissance Italian Unification

Both changes aren't going to resolve the core of the problem : not enough ressources or money. Really, it's simple as that, whatever the result of the war with Florence, Milan was in a financial dead end.

I don't believe it was as bad as you say. Sure they were pinched, but not so bad as to be paralyzing. But let's say it was. Even if it were, loot from Florence and exactions from Genoa would've taken of any financial shortfalls--if any.
 
I don't believe it was as bad as you say. Sure they were pinched, but not so bad as to be paralyzing. But let's say it was. Even if it were, loot from Florence and exactions from Genoa would've taken of any financial shortfalls--if any.

1) Even his widow was personally broke. How are described his treasury is "drained". It's the main reason the operation against Florence were slowed down. They weren't paralyzed, but clearly Gian Galeazzo reached the limits of its ressources. I found highly doubtful he could have

2) Florence had to use particularly harsh taxes to fund the war. They had a treasury in an even worst situation than Visconti. If Milan expected to fund its expansionnism with Florence's loot, they wouldn't had gone far.
 
I'm pretty doubtful that Gian Galeazzo was in financial difficulties.
After all he was the lord of the best agricultural lands in western Europe (lands whose productivity had been even increased by the great irrigation canals sponsored by him) and controlled all the major traffic routes from northern Italy to Germanies and Flanders (which is another way to say that most overland traffic to and from Venice was routed through his lands and paid duties to him).

The larger financial expenditures were also well beyond him by 1402 (I'm talking of the bribes to the HRE to be invested with the ducal title, but also the above mentioned irrigation canals and the drainage of marshes). He had also been re-organizing and improving his chancery and the tax collection (as a matter of fact the first serious census of land properties in Lombardy was commissioned by him).

The siege of Florence was not really very long, considering the difficult terrain protecting the city and the fact that he waited for the surrender of Bologna before investing in earnest Florence. In the last few years he had also become lord of Perugia, Assisi, Nocera, Gualdo Tadino, Spoleto: it's practically all of modern Umbria, and it does not convey the impression of a lord in financial straits.

It's quite true that even after the fall of Florence there are still quite a few independent lordships or free cities in Italy (Savoy, Montferrat, Saluzzo, Genoa in the west; Mantua, Padova, Ferrara, Ravenna, Ancona and Montefeltro in the east, just to mention the most important ones). Note that I do not include Venice or Naples: the Serenissima is the golden goose for the duke of Milan, it would be silly to kill or maim it trying to conquer the city; the kingdom of Naples will require a major effort if it is really to be taken and I believe that it will be a matter that will have to wait one or two generations to be settled (but it is quite likely that from his holdings in Umbria GG will still play his little subversion games with the lords of Abruzzo and Puglia). My guess is that a GG surviving the plague of late 1402 will take a few years to consolidate and re-organize his lordships (except maybe a short campaign against Padova and aiding and abetting his Malatesta allies and vassals to settle their long-standing feud with the Montefeltro). The years up to 1410 should be quiet ones: afterwards the dynastic crises in Aragon and France should open a lot of juicy possibilities.
 
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