11 years is a big age gap, especially when its the woman who is 11 years older. As I have stated elsewhere, Mary's mother and grandmother had their final pregnancies in their early 30s. Her best years for child bearing were in her teens and 20s. Mary has superb relations, however her primary role was to produce heirs.
I don't think your ideas for the husbands of all the girls are realistic at all. It seems you've just looked at wikipedia for age appropriate candidates and given no further consideration. You've probably shot yourself in the foot by being too ambitious, there's no need for Henry to have 9 surviving daughters, 4 or 5 would have been more interesting and achieveable.
When I look for ideal husbands, I look by relations to the women, rank and yes age, as you said above they need to be close and I have never liked the idea of marrying women off to an old emperor who is near deaths door, just so he can try and produce one last heir while she can claim a downry as the widowed emperess.
As for ambitiousness, yes maybe i did keep 4 or 5 girls a live more then what was needed, but the thought of any daughter dying would kill my interest, where as i wondered what the 9 daughters of Henry would actually do.
Why would a Portugese prince want to marry a daughter of Anne Boleyn? What does he get out of it? A Portugese prince is going to look first for a Catholic bride, with a big dowry, the traditional option was a Habsburg princess, there were plenty of them around. Henri II of France had shown that marriage to a wealthy heiress, not strictly of royal birth was also a good option for a younger son.
Anne has just show she has child bearing hips, with 7 healthy children being born, any daughter of Anne, who not strictly of royal birth, was still the Queen of England.
The problem with a Habsburg princess is there closeness to Spain who
REALLY is the sworn enemy of Portugal, not just the main.
Why would the son of the King of Denmark want to marry an English princess, when her sister had just married the Swedish's king's son? England's alliance with Sweden would be undone with an alliance with one of Sweden's main enemies, Denmark. The two are contradictory.
There has been peace between these two nations since 1521. A war, King Frederick I of Denmark was not a part of. These two kings would look for an alliance and with 9 daughters, England would be the place to go.
I think your idea about Russia is frankly ASB. You might as well imagine that one of Henry's daughters marry a Japanese or Indian ruler.
How is it ASB, Elizabeth and Ivan IOTL had great relations and at the time Russia was emergining as the new Empire with a large military and natural resources, Henry would be looking to trade more with Russia and the best was to secure a good trade flow is to have one of his daughters marry the Tsar. If the family has already changed from Catholic to CoE, one more religious convert wont make a difference.
While un-heard of Japan and India is stupid. If you are going to compare it to anything I would have at least thought you would have said the Turks or Barbers.
Why would Edward VI marry a Catholic? You do realise he was a Protestant fundamentalist right?
You can have a protestant married to a catholic, its not against the law, as long as both are happy, which I can see these two be with Anne being raise by her father, who was sympathetic to Lutheranism.
Your premise is messy and there is no consistency.
When is History ever consistent? It cant be predicted and is never simple.