The trouble with any of the matches England proposed under Edward IV wasn't that he didn't want to spend the money, but that they probably couldn't even if they wanted to. Edward IV didn't accept France's tithe because he was lazy, but because the English coffers were getting very lean during this time. Under Henry VI of England and Marguerite of Anjou, there had been massive economic mismanagement, and while this had been minimized under the Yorkist regime (Elizabeth Wydville had, initially, less than half the staff that her predecessar had kept), England was in such a position that upon negotiations with Burgundy for a match between the Princess Anne and Philip of Burgundy, they still hadn't paid most of Margaret of York's dowry. The betrothal between Elizabeth of York and the Dauphin was, in part, built upon the idea that England could prevent another war, end the questioning of the new regime, and get rid of a princess for nothing, all in one move. The Cecily match was essentially the same thing. The trouble is that no other countries were as unfortunate in position as France and Scotland, and even in those cases France decided that they'd rather play nice with Burgundy than spend a fortune on Edward.
Had Edward lived, say, another decade, it's hard to say what would have happened. On top of the possibility of more children (Elizabeth Wydville was about 42/43 when Bridget was born, her mother had her final child around the same age if not a year or two older, and she was even considered briefly as a bride for the King of Scots in her widowhood, where it was claimed she was still capable of bearing children), the political climate of Europe shifted to much during this time it's hard to say what might have happened. One thing you can be pretty sure of is that Charles VIII of France is going to have to marry Anne I,
Duchess of Brittany in order to prevent her from ending up elsewhere, so that leaves Margaret of Burgundy free to marry elsewhere. While I can definitely see her still ending up in Spain, it's equally likely her step-grandmother will push for England. If that happens, I can't see a doubly match between Anne and Philip, and quite honestly there 's difficulty in predicting where everyone ends up. Here's some potential matches that could end up getting pushed through:
- Elizabeth of York (b.1466) m. Manuel I of Portugal (b.1469)
- Now we know France is going to fall through, and in my opinion I can see Edward IV getting annoyed as the Emperor and King of France fight over Anne of Brittany, who was meant to be his son's bride. Portugal is a safe bet for England, Manuel is the right age, titled and close to the throne. It isn't the grand match initially envisioned, but a strong one from most perspectives. The fact he ends up King of Portugal is a fun twist.
- Cecily of York (b.1469) m. James IV of Scotland (b.1473)
- Not much to say. It was in line to happen before her father died, the Scots only ended it when she was declared illegitimate and once there was a new English Princess they didn't want the old one.
- Edward V of England (b.1470) m. Margaret of Burgundy (b.1480) or Isabella of Aragon & Castile (b.1470)
- I can see this going two ways. Either Margaret of York gets her way and her step-granddaughter is married to her nephew, or Edward gets greedy, and his daughter is able to convince the recently widowed Isabella that her brother is great, she's too young to mourn forever and England is great. I'd probably lean towards Margaret of Burgundy here but it'd depend on what you wanted to happen.
- Richard, Duke of York(b.1473) m. Margaret of Burgundy (b.1480), or an English heiress such as Anne St. Leger (b.1474), or Bianca Maria Sforza (b.1472)
- While a foreign match is possible, I do see them trying to get him another heiress. If they can find one is another discussion, but let's say upon Edward's death in the 1490s Richard is probably unmatched.
- Anne of York (b.1475) m. Maximilian I, Holy Roman Emperor(b.1459)
- This is probably the only match I could see happening in the long run, although I'd be interested in any other options. But in the time between Anne of Brittany is married off to France and when he married Bianca Maria Sforza IRL, I could see an English match happening if just because he'll want to cement the alliance against France again.
- Catherine of York (b.1479) m. Philibert II, Duke of Savoy (b.1478) or Edward Plantagenet, Earl of Warwick(b.1475)
- It's hard to say what might happen here, but I thought that Savoy would be a solid match, particularly after Bona of Savoy was snubbed by Edward years prior. If not Savoy, I could see a domestic match to the Earl of Warwick, maybe following her father's death in order to welcome him back into the family fold.
- Bridget of York (b.1480) m. God (b.????)
Now some of these are probably stretches, but I think that unless we see all the Princesses off like Bridget, we'll see them married off in around the 1490s.