Thoughts based off the discussion so far:
Henry VIII of England (b.1491: d.1547) m. Catherine of Aragon (b.1485: d.1536) (a), Anne Boleyn (b.1501/1507: d.1536) (b), Jane Seymour (b.1508: d.1537) (c), Anne of Cleves (b.1515: d.1557) (d), Catherine Howard (b.1523: d.1542) (e), Catherine Howard (b.1512: d.1548) (f)
- Mary is still gonna end up with Philip, if she can't marry the Emperor himself.
- Any of the candidates not married to Mary is gonna be offered Elizabeth, and for the sake of what people have suggested in the chat, I'd probably go with the Duke of Beja. Keeps Portugal independent and gives Elizabeth something to do once Luis dies in 1555. If she's got children, she's gonna want them to rule.
- Jane Grey might be offered outwards from England, but most likely she either marries an English Nobleman, or into Scotland, to secure that alliance. It might be funny if she ended up with Lord Darnley as part of a larger plan for Mary to influence Scotland, while also rewarding her faithful cousin.
- Don Carlos is gonna end up married to Elisabeth of Valois (or another bride, depending on how the Spanish and French act towards each other. Say, if they marry in 1559, while Philip could theoretically be mourning Mary (maybe they're closer with the birth of children) then you could easily get a son by 1568.
Henry VIII of England (b.1491: d.1547) m. Catherine of Aragon (b.1485: d.1536) (a), Anne Boleyn (b.1501/1507: d.1536) (b), Jane Seymour (b.1508: d.1537) (c), Anne of Cleves (b.1515: d.1557) (d), Catherine Howard (b.1523: d.1542) (e), Catherine Howard (b.1512: d.1548) (f)
1a) Stillborn Girl (c.1510)
2a) Henry Tudor, Prince of Wales (b.1511: d.1511)
3a) Henry Tudor, Prince of Wales (b.1513: d.1513)
4a) Henry Tudor, Prince of Wales (b.1515: d.1515)
5a) Mary I of England (b.1516: d.1558) m. Philip II of Spain (b.1527: d.1598) (a)
6a) Stillborn Daughter (c.1518)
7b) Elizabeth Tudor (b.1533: d.1604) m. Luis of Portugal, Duke of Beja (b.1506: d.1555) (a)
8b) Stillborn Son (c.1534)
9b) Miscarriage (c.1536)
10c) Edward Tudor, Prince of Wales (b.1537: d.1546)
2a) Henry Tudor, Prince of Wales (b.1511: d.1511)
3a) Henry Tudor, Prince of Wales (b.1513: d.1513)
4a) Henry Tudor, Prince of Wales (b.1515: d.1515)
5a) Mary I of England (b.1516: d.1558) m. Philip II of Spain (b.1527: d.1598) (a)
1a) Henry IX of England, Sovereign of the Netherlands (b.1549)
2a) Stillborn Son (c.1550)
3a) Miscarriage (c.1552)
4a) Philip Tudor-Hapsburg, Duke of York (b.1554)
2a) Stillborn Son (c.1550)
3a) Miscarriage (c.1552)
4a) Philip Tudor-Hapsburg, Duke of York (b.1554)
6a) Stillborn Daughter (c.1518)
7b) Elizabeth Tudor (b.1533: d.1604) m. Luis of Portugal, Duke of Beja (b.1506: d.1555) (a)
1a) Joan of Beja (b.1550)
2a) Luis I of Portugal (b.1553)
2a) Luis I of Portugal (b.1553)
8b) Stillborn Son (c.1534)
9b) Miscarriage (c.1536)
10c) Edward Tudor, Prince of Wales (b.1537: d.1546)