In OTL Arthur, Prince of Wales and Catherine of Aragon got sick not too long after their wedding in 1502. While Catherine recovered, Arthur died in that same year. But What if Henry, Duke of York (OTL Henry VIII) also caught the unspecified Illness and died in 1503?

1. This leaves Margaret, Queen of Scotland heir presumptive to the throne
2. Henry VII is a widower
3. He was also going to attempt to marry Catherine of Aragon
4. Having a queen in those times was associated with Civil War (ie. The Anarchy)
5. Margaret is already married to James IV of Scotland
6. If Margaret isn't displaced it might mean a union between England and Scotland

If Henry VII dies on schedule in 1509, what would happen when Margaret ascends the throne and becomes the First (Undisputed) Queen of England? Or would Henry VII try to get remarried?
 
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Oh, he will remarry. Possibly to Joanna of Naples. While Henry VII did not fear Anglo-Scottish union, he would still try to have a son
IMO, there is a very good chance he’ll remarry to Katherine of Aragon. She’s already in England, of marriageable age, has Lancastrian blood, it upholds the alliance with Castile and Aragon (since Isabella is still alive at this time it has more strength), and she’s claiming to still be a virgin, so he could get a dispensation. And it solves two birds with one stone: Henry needing a wife, and the issue of Katherine’s widow status.

With young Henry dead and Henry VII having no other surviving sons, I can also see Ferdinand being much more receptive to this proposal than he was OTL since ITTL Henry VII and Katherine’s son would be king.
 
Assuming, Elizabeth of York dies on schedule, Henry VII is definitely remarrying, probably to Giovanna of Naples. Any son of theirs lacks Yorkist blood which could be an issue. Maybe the son could marry a Yorkist descendant, such as Ursula Pole or Margaret Courtenay? Alternatively, Henry VII could marry Margaret Plantagenet herself since she’d only be 31 when her husband dies in 1504. I think if he remarried to either of them he could manage to sire a son. Any Regency for a son would probably be headed by Margaret Beaufort initially, before being passed down onto the Duke of Buckingham (by virtue of being the sole Duke in the realm and a trusted ally). In the interim he would move to insure Margaret and James’s peaceful ascension to the English throne (he was fine with them becoming monarchs in otl).
 
What are the chances that henry tries to marry catherine of aragon, if it is decided that her marriage to arthur was unconsummated? her mom would oppose this but...
 
4. Having a queen in those times was associated with Civil War (ie. The Anarchy)
The Anarchy was four hundred years ago by this point. I know it gets brought up a lot in these discussions, but four hundred years is plenty of time for attitudes to change, and given that Mary and Elizabeth were both able to take power and rule until the ends of their natural lives, I don't think Margaret will have much trouble becoming Queen, particularly as she's got a husband to fight any rebels on her behalf and is backed up by the resources of Scotland (which aren't as great as the resources of England, but aren't negligible either, and could easily tip the balance if a civil war were to break out).
 
Now i'm interested in this early anglo-scottish union. What if Henry VII died a little early and didn't marry/didn't have a child? How would Margaret's reign be?
 
Wasn't Isabella the one more opposed to it?
Yes,
What are the chances that henry tries to marry catherine of aragon, if it is decided that her marriage to arthur was unconsummated? her mom would oppose this but...
Here she would have no reason to oppose the match (as she seriously take in consideration a match between Maria and Vladislaus II, who was around Henry VII’s age, so the issue was Henry having a living son who would be a better match for Catherine and guaranteed who Isabella‘s grandson would be King)
 
Here she would have no reason to oppose the match (as she seriously take in consideration a match between Maria and Vladislaus II, who was around Henry VII’s age, so the issue was Henry having a living son who would be a better match for Catherine and guaranteed who Isabella‘s grandson would be King)
How would she feel about her daugher marrying her ex-husband's father? Even if the first marriage was never consummated, that's still a bit icky.
 
How would she feel about her daugher marrying her ex-husband's father? Even if the first marriage was never consummated, that's still a bit icky.
If the marriage was never consummated then catalina is not his daughter in the eyes of the church and the wedding could happen (not sure if it would require a dispensation but that can easily be gotten)
 
How would she feel about her daugher marrying her ex-husband's father? Even if the first marriage was never consummated, that's still a bit icky.
She comes from Iberia, where close kin relationships were common. Her brother was due to marry his half-niece so I don’t think it’d bother her too much, especially once the Pope grants the dispensation (iirc, one was requested just in case the marriage was consummated).
 
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