@Brita can correct me, but wasn't the clause about Anne marrying Charles' successor only in the event that she and Charles had no (male) issue. Ergo, if Charles-Orland had survived she and Louis wouldn't have married?
Yeah, but in this case she would need to stay in the French royal domains, as Charles-Orland would succeed the throne and historically french queens who were mothers of the king would not return to their home countries.
@Geoffrey1016: to compare Anne and Mary of Scots is pretty pointless. The two were very different scenarios. Brittany was "seen" as part of France (although much like the Lorrainers or the Burgundians, they tended to dispute this point), Scotland never was. IIRC Anne's independence of action as duchess was severely curtailed by Charles (to the point of pettiness, he refused to allow any Breton appointments without his say so, Anne was not allowed to receive Breton representatives alone but
with Charles etc), whereas Louis only seemed to interfere in Breton affairs when it was necessary. He permitted Anne to run the place by herself, rarely meddled in her appointments (and only when it directly contradicted France's interests) and seldom "forced" her to change her policies (one example of it is Claude's betrothal to Karl V or her willing Brittany to Renée de France when Claude married François d'Angoulême). If we're going with a Mary, Queen of Scots' analogy, Charles is a combo of Darnley-Bothwell rather than her Valois husband.
From
my thread on Anne marrying Philipp of Burgundy
Since the analogy was raised in Retha Warnicke's biography of Mary Queen of Scots, in which she said that Scots at the time worried that Scotland would become the next Brittany at the time when the Scottish Parliament approved the appointment of commissioners to give Francois the Dauphin crown matrimonial of Scotland, which aroused my idea to compare these two tragic young female rulers who happened to marry a King of France during their teens.
Anne was only one year older than Philip the Fair, and Charles VIII was 7 years older than Anne. Catherine was one year older than Arthur, Prince of Wales, and Francois II was 2 years younger than Mary Queen of Scots, so a royal marriage that involved a slightly younger husband would not be that unusual. If Anne was betrothed to Philip in 1488 and the marriage was concluded in 1494, the same year Maximilian married Bianca Maria of Milan, then Isabella and Ferdinand would try to find another royal ally for a match with Joanna of Castile.
If Anne concluded her marriage with Maximilian in 1494, then Philip could marry Joanna as OTL, which would, however, arouse Charles VIII and Anne de Beaujeu's nerve again, as France would now be surrounded by Habsburgs on four sides if Juan, Prince of Asturias and Girona, died as OTL. The French court might declare Flanders and Artois(both of which were largely French fiefs, although Flanders was the composite of an Imperial fief and a French fief) forfeit, but would likely receive a sounding defeat.
I agree with you that Charles VIII behaved more like Lord Darnley or Earl of Bothwell than Francois II, though, since Francois II was too sickly and stuttered to say "Non" to anything Mary and her mother would might work out about Scotland.