I'd personally go for something before England gets too Protestant. In a crazy-ass world, maybe the Duke of Berwick could conquer Britain under the auspices of Felipe V, but that's pretty ASB. Fun, though!
The Mary-having-a-son possibility is likely unworkable. Firstly because Britain would almost certainly become a secundogeniture, provided there were enough princes. Secondly because the Spanish Habsburgs would be hard pressed to survive with their history of inbreeding (although they might marry into British noble houses to pacify the nativists). Thirdly because of Protestantism, as previously mentioned. Fourthly because the English would never settle for being ruled by an absolute monarch across the Bay of Biscay, given their isolationism and penchant for Parliaments. A Spanish Armada scenario would probably fail for similar reasons.
A fifteenth century personal union would be the optimum solution, IMO. A prerequisites of this would seem to be a Lancastrian victory in the Wars of the Roses, the death of Edward of Westminster without issue and the exclusion of the Beauforts from the line of succession. The Beauforts didn't really have a candidate between the extinction of the male line in 1471 and the rise of Henry Tudor.
Therefore, someone like the Duke of Exeter could ask for Spanish assistance in a War of the Roses rematch sometime before his death in 1475 in return for naming Enrique IV or los Reyes Catolicos his heirs (his closest male relations at the time were the teenage Earls of Westmorland and Kent, and one of Gaunt's daughters married into the Castilian royal family). If this expedition succeeds and everyone keeps the agreement, then Isabella and Ferdinand become monarchs of England in the mid-1470s. For extras, this combined empire could either conquer Scotland and Portugal or get them by marriage. Portugal is easy: just have Miquel de la Paz survive. This would also butterfly or delay the Habsburg inheritance, of course - I'm sure France would have something to say about being completely surrounded by their lands!