WI: Joanna 'The Mad' and Philip of Habsburg had two other sons?

I brought up Eleanor because in OTL Maximilian I and his daughter Margaret tried to betroth her to Henry VIII. Henry VII liked the idea but upon his death, Henry VIII married Catherine rather quickly. Philip may have been able to convince Henry VIII to marry Eleanor. An alliance between England and Burgundy would definitely make sense for both kings. And if Philip was tolerant of Luther, Charles V might take advantage of that and take control of the Spanish kingdoms away from dear old “heretic” dad.
 
And if Philip was tolerant of Luther, Charles V might take advantage of that and take control of the Spanish kingdoms away from dear old “heretic” dad.

Philip then might feel betrayed and turn to his Austrian younger sons Ferdinand, Maximilian, Philip TY (and why not) Ernst and Henry. Hungry for power, maybe the quintet of losers gets tired of the fowardness and authority of Charles and tries to overthrow him...

As for daughters, supposing Eleanor marries Henry VIII, Isabella still marries Christian II, Mary marries Louis II of Hungary and Catherine still marries John III of Portugal just as IOTL, would there be any other powerful royals available? The hypothetical Margaret could be given as a second wife to a widowed King Francis, but how about Beatrice? If she is born between 1515 and 1520, she could be a bride either for James V of Scotland or maybe Sigismund II Augustus of Poland. Which match would be the most viable and desirable from the Habsburg point of view?
 
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By the way, I know this topic revolves around the Point of Divergence of Joanna of Castile-Aragon and Philip of Austria-Burgundy having even more children than they had IOTL, but I'd like to invite you to make a brief break and think about a scenario in which things developed otherwise and the couple had no male children at all, with Philip dying in 1506 as IOTL.

In this case, I'd like to make some questions regarding the inheritance:

1 - As the eldest daughter to Joanna and heir to Castile and Aragon, who would Eleanor marry? Would she marry Henry II of Navarre in order to annex the Navarrese lands (including the lands north of the Pyrenees) permanently to the Trastámara crowns?

2 - If she doesn't marry Henry, the "weakest" of suitable king-consorts, who would she marry then? Marrying her off to Francis I of France would create a bizarre French-Spanish personal union that probably would lead to bloody consequences. If she marries John III of Portugal, this marriage would make the infamous Iberian Union happen decades earlier. Suggestions?

3 - The Habsburg crown is only passed through the male line, with women excluded from inheritance. The only extant male line of Habsburgs during the early years of Charles V and his siblings was his own. In the absence of male grandsons, would Emperor Maximilian I maybe issue an edict on behalf of his granddaughter Mary and her husband (Maximilian's adopted grandson) Louis II of Hungary in a fashion similar to the Pragmatic Sanction of 1713, granting them the succession and inaugurating the Jagellon-Habsburg Dinasty, fusing Austria-Burgundy to Hungary and Bohemia?

4 - What would be the role of Isabella of Burgundy and Catherine of Austria in this complicated situation?

The die has been cast!
 
In the event of Philip only having daughters, Eleanor would inherit Burgundy upon his death. Eleanor would be heir to Joanna’s thrones and the most sought after bride in Europe. Eleanor would also be heir to her grandfather Maximilian’s Austrian possessions. Maximilian would likely seek to split his inheritance between his other granddaughters but Eleanor may refuse to renounce her succession rights to his lands in TTL. A marriage to John III would be the most logical choice for Eleanor.
 
In the event of Philip only having daughters, Eleanor would inherit Burgundy upon his death. Eleanor would be heir to Joanna’s thrones and the most sought after bride in Europe. Eleanor would also be heir to her grandfather Maximilian’s Austrian possessions. Maximilian would likely seek to split his inheritance between his other granddaughters but Eleanor may refuse to renounce her succession rights to his lands in TTL. A marriage to John III would be the most logical choice for Eleanor.

If Eleanor, much like Charles, is unwilling to divide her inheritance amongst her sisters, is it possible that after marrying to John III and producing issue she finally divides the Iberian kingdoms? I mean, a personal union in which we have "Habsburg Dominions > Portugal" would lead to mass dissatisfaction, mainly from high Portuguese nobles such as the dukes of Braganza. This seems to be a great timeline, but I'd rather work it out in another topic.

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Back to the main "The Great Habsburg Sausage Party" Timeline, I enlisted superficially the possessions held by the Habsburg crown around OTL 1550's, and if it wasn't for damn laws of absolute-undeniable-land-concentrating-male-primogeniture, there would be enough places to be ruled by different sovereigns.

As follows:

The Crown of Castille:

1. Castille proper
Not much to say about it, the central-western section of Iberian peninsula (except, obviously, for Portugal) including also the lands of the former Emirate of Granada.
2. The Overseas Empire
There were the Vicerroyalties of New Spain, Peru, New Granada, Capitaincy of Chile, The Spanish East Indies and more... Any chance of turning those territories into hereditary vicerroalties governed by an European Habsburg prince (or maybe princes)?

The Crown of Aragon:

3. Aragon-Catalonia-Valencia-Balearic Islands proper
Self-explanatory.
4. Duchy of Milan
Actually the Duchy of Milan belonged to the already unified crown of Spain after the fall of the Sforzas OTL.
5. Kingdom of Sardinia
Eventually, OTL, would become an independent sovereign kingdom united to the Duchy of Savoy. What would be effects of granting Sardinia an earlier independence (under the house of Habsburg)?
6. Kingdom of the Sicilies (Naples and Trinacria)
Would also become independent, but under the Bourbons. Same question as above.
7. Southern Navarre
Could have its north-Pyrenees area conquered by force or maybe by another traditional diplomatic marriage. Or maybe everyone keeps okay with this, after all it's the largest part of the Navarrese territory.

The Crown of Burgundy:

8. The Seven Dutch Provinces
The division between Northern/Protestant and Southern/Catholic Netherlands would only strictly make sense in the context of the Dutch Revolt, but implying that as OTL it happens, there wouldn't be any chances of maybe keeping a Habsburg heir in power, conciliating the Protestant interests or perhaps offering a hypothetical daughter to William the Silent to keep the dinasty alive? Although not properly Habsburgs according to agnatic traditions, at least this latter setting would prevent a greater severance between the Dutch and the Spanish/Austrian.
9. Southern Catholic Netherlands and Luxembourg
Again self-explanatory. Maybe they start calling it "Belgium" centuries earlier.
10. The Franche-Comté
Any chance of Habsburgs preventing its slow-but-effective annexation by France? Butterflies (and LSD): an unification between Lorraine and the Franche-Comté? Oh wow, very, very far-fetched...

The Crown of Austria:

11. Austria Proper (Lower and Upper Austria)
The headquarters of the germanic Habsburgs and the german crown. Not much to say about it, besides that it's the most important area of Austria at the time.
12. Inner Austria (Styria, Carinthia and Carniola)
Another traditional appanage given to the non-first-borns.
13. Tyrol and Further Austria
The most irrelevant of all, but its proximity to the northern Italian duchies could lead to interesting alternative settings.

What can we do with all this now? Seriously leaving it all to one or at most two monarchs? Please add information and correct me if I'm wrong about something!
 
I've decided, also, to create a small timeline listing the births of the many children of Joanna and Philip, in a setting in which he lived up to the 1520's thus being able to impregnate her over and over until menopause. As follows:

1498 - Eleanor of Austria - A suggested bride to Henry VIII, maybe a second bride, following the death of her aunt, Catherine of Aragon.
1500 - Charles V, Holy Roman Emperor - The stubborn and self-centered absolutist we all love.
1501 - Isabella of Burgundy - As IOTL, the ambigously Catholic/Protestant teen wife of Christian II of Denmark, Norway and Sweden.
1503 - Ferdinand I, Holy Roman Emperor - ... Holy Roman Emperor? King of Aragon? King of Naples-Sicily? You decide.
1505 - Mary of Austria - Even more powerful than IOTL, since ITTL Louis II of Hungary would survive long enough to produce heirs and maybe be elected king of Poland.
1507 - Catherine of Austria - As IOTL, a wife to John III of Portugal. Maybe she's luckier in this timeline as sees all of her offspring grow into adulthood instead of only two sickly infantes.
1508 - Maximilian of Austria - The favorite grandson of Maximilian I, the archduke of Tyrol, the Duke of Milan... Many options.
1510 - Margaret of Burgundy - Maybe a second wife to Francis I of France, after the death of Claude of Brittany?
1512 - Philip the Younger - Perhaps as politically skillful and charismatic as his father... Maybe hated by Ferdinand II as his father... Who knows?
1515 - Ernst of Austria - ????????????
1516 - Beatrice of Burgundy - She would have the same age of IOTL Marie the Guise. James V of Scotland would probably look for a better ranked wife if he had the option.
1518 - Frederick/Henry of Austria - I have absolutely no idea. Probably a bishop.

Now... What follows?
 
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