In OTL, the same anxiety which spurred Henry VII on to six different marriages seems to have restrained him from marrying his children off in any great haste. While there were several betrothals at different intervals, including famously that between the then-Princess Mary and Charles V which was broken off by Charles, Henry seems to have shied away from the very real possibility of marrying off his eldest daughter in her early teens and procurring a male heir through her (all Julio-Claudian-like, by annexing a potential son-in-law as a stand-in adoptive son and presumptive crown prince, and, in the long run, through him and her, female-line grandsons).
The possibility of uniting Mary (born 1516) with cousins such as James V of Scots (born 1512), Henry Courtenay, 1st Marques of Exeter (born c.1498) or else his son Edward Courtenay (b.1527), Henry Stafford (b.1501), son and heir of the last, overmighty Duke of Buckingham, or Henry Pole (c.1492), Lord Montague, son of the Countess of Salisbury, or even Thomas Manners, later 1st Earl of Rutland, all of whom were rich in Plantagenet blood and would offer Henry a sound presumptive heir and line of succession. Henry would, quite naturally, have almost absolute control over such a match and its offspring, to raise and promote as he saw fit.
Scottish noblemen and heirs presumptives such as John Stewart, 2nd Duke of Albany, James Hamilton, 2nd Earl of Arran and Matthew Stewart, 4th Earl of Lennox also have their merits.
The possibility of uniting Mary (born 1516) with cousins such as James V of Scots (born 1512), Henry Courtenay, 1st Marques of Exeter (born c.1498) or else his son Edward Courtenay (b.1527), Henry Stafford (b.1501), son and heir of the last, overmighty Duke of Buckingham, or Henry Pole (c.1492), Lord Montague, son of the Countess of Salisbury, or even Thomas Manners, later 1st Earl of Rutland, all of whom were rich in Plantagenet blood and would offer Henry a sound presumptive heir and line of succession. Henry would, quite naturally, have almost absolute control over such a match and its offspring, to raise and promote as he saw fit.
Scottish noblemen and heirs presumptives such as John Stewart, 2nd Duke of Albany, James Hamilton, 2nd Earl of Arran and Matthew Stewart, 4th Earl of Lennox also have their merits.