It's fun to woo the hawt Spanish senoritas but I always thought it would be cool to be able to woo Indian princesses and Pirate Princesses.
That's a good point. While a beautiful governor's daughter should probably still be the "best" wife score-wise, it would be neat if you could also woo serving wenches, merchants' daughters, chiefs' daughters, etc. Maybe they could change it so you get the best score for the prettiest woman in the Caribbean regardless of her social standing. Then every game would be a little different. You already have to rep grind, so to speak, to have a chance with the beautiful governors' daughters, so they'd need to add ways to rep grind for the others. Wealthy merchants would be impressed if you played the trade side of the game well (and they should really add pirate attacks on your own ship if you have valuable cargo), and serving wenches might just go by your notoriety, though that seems a little thin by comparison. They'd have to add a whole new way to play the game to earn credit with the natives, probably.
It would also be fun if the gifts the girls gave you differed. Only the chief's daughter could give you the medicinal herbs that extend your life, but she wouldn't have access to the pistols, for example.
Plus no matter how much I tried to reconquer the Spanish Main for Mother Spain it felt that little was legitimately done when I did convert most of them over.
That's because Spain already owns 90% of the major ports. Quit being such a loyalist. I conquered everything for Holland once, and that really changed the feel of things. There were fluyts everywhere, all with names I couldn't pronounce.