Hmm, that makes sense I suppose. That said, even if Florence submits, that does not remove Florence (and the other larger than average states) as a potential threat. In GG's shoes, I'm not sure I'd feel safe extending my rule down there so soon after capturing so many other major territories. (He does have 13-15 years to grab the rest though, so I guess it's not that great an issue)
That only applies to the unaffiliated ones though. I wasn't aware of the politics in the area at the time, and it does indeed sound like it would make sense for some of those territories to fall to GG indirectly after beating down their allies or helping them against their foes.
Shame that the basemap I used (the same you posted earlier in the thread) doesn't show that part of Italy in any real detail though. If I don't find a better one, there's only a few I'll be able to label accurately.
After the Florentine surrender, there will be a podesta' appointed by GG as highest office holder in Florence, and a Milanese garrison. That should be enough to keep the Florentines to their side of the bargain. Not to mention the positive hate of the other Tuscan cities (with Pisa and Siena in the frontline) for Florence.
On a more positive side, the central administration and the rationalization of taxes and duties which had been started by GG OTL (and should be completed by him ITTL) should be a big incentive for the merchant and banker class to play ball.
This would work also for the other cities too, obviously. AFAIK, the cities and towns grabbed by GG were never wrung dry, nor were excessive political reprisals allowed.
Asfar as the Marches of Ancona are concerned, I'm becoming more and more convinced that GG would use his old allies, the Malatestas, as viceroys, maybe even resurrecting the old Carolingian title of Wardens of the Marches of Ancona (but Ancona itself - as along standing free republic and the chief harbor on the Adriatic - would probably be ruleddirectly by him through a podesta;
Resurrecting the old ducal title of Tuscany might also be a possibility at some point.
A crown is not guaranteed even if the Visconti state remains stable, but it's certainly a possibility if the political climate of Europe allows it, aye. Would it be a Guelph or a Ghibelline crown though? It's kind of troublesome when both of the men who could grant you a crown happen to have reasons to be hostile towards you. I could even see the Pope resort to talking about a "new Lombard threat" and allying with the Emperor against the Visconti further down the line.
Which pope? at the moment there are two incumbents, one in Rome and one in Avignon, and if things do go on for a few years as per OTL there is a good chance a third one will be appointed too. Plenty of elbow room and opportunity for the wily GG. OTOH the emperor is in a penurious state and always in need of money. Which is another nice thing for the newly created (and very solvent) duke of Milan. My idea is that GG will negotiate/buy/extort whichever title will be available from both sides (and will play a major and well rewarded role in the composition of the schism). Remember that France will soon be embroiled in the 100 years war again, and the Aragonese will get into a dynastic squabble by 1410, as Janprimus pointed out: it would be difficult to paint a more favourable scenario for a surviving GG
Hm, so they're natural allies for economical reasons rather than purely political and/or military ones? I suppose that makes some sense from Venice's viewpoint, at least. Wouldn't GG, or another Visconti in the future, see Venice as a valuable city to own rather than to trade with though? Or would they realize that even if they do capture the city, they might risk shattering or at the very least redirecting Venice's old trade network? I am not sure how far your average (or not so average) Italian nobleman thought ahead in terms of trade and economic power at the time, so I'm not sure.
I am not saying they will be allied forever. I'm just pointing out that there are sound commercial reasons to cooperate and no real-life reason to be on opposite camps. In a couple of generations this may change, or maybe not. What I know is that both the Visconti and the Serenissima would benefit in a major way by cooperating with each other, and that GG is well above the average run-of-the-mill petty prince.
Speaking of politics, would GG or a future Visconti be interested in expanding into Naples? I could see the Visconti do what Filippo Maria Visconti did OTL and agree on a north/south split of Italy with the northern part going to them and the southern part going to Aragon, but if memory serves that agreement only came around as the result of a series of rather unlikely events. The Visconti would certainly have reason to dislike the idea of entrenched French influence in the area, but I am not sure if they would see Aragon as a much better option. Conquering it themselves seems like it would be difficult though.
Probably yes. Actually I should say most certainly.
GG still remembers when the Aragonese crown vetoed his marriage proposal to Maria of Sicily (and sent a fleet to harass the Pisan ship he had despatched to bring the queen to North Italy). Then there is the troubled times the kingdom of Naples is going to live in the next couple of decades, as well as the above mentioned Aragonese dynastic crisis.
A lot will depend on the settlement of the schism (the pope is still the formal overlord of the crowns of Naples and Sicily), and what GG can get out of the settlement.
It should be also mentioned that the Genoese mercantile interests would be very opposed to an Aragonese expansion in southern Italy (and IOTL Filippo Maria Visconti supported the intervention of Renee d'Anjou for this very reason).
Obviously ITTL GG would be in a much stronger position than his son was IOTL, and his strategy would be different. He might even push for his younger son (said Filippo Maria) to marry Joan of Naples (the bride would be quite older than the groom, but it has never been a major obstacle in dynastic marriages) which would unite the kingdom of Naples with the Viscontean holdings. Alternatively he might look for a fight against the Aragonese in the kingdom of Naples (mainly by subversion) and in Sardinia (leveraging on the old Visconti claim on the Judicate of Gallura, which came from the Pisan branch of the Visconti, as well as on the Genoese strongholds in Corsica and Northern Sardinia and supporting the still independent Judicate of Arborea). There could even be a royal crown in this, possibly even two. Note that Venice would certainly be happy to support naval operation against Puglia.