Any privateers in the Caribbean would be able to draw on a number of Native sailors. Sure, they're experienced with different kinds of ships, but their knowledge of navigation and willingness to put out to sea means that English and French privateers could find themselves with largely Native crews-and said crews would be learning all kinds of useful things about European technology, weaponry and culture, which could be useful for their homelands.
Imagine European-Native privateer groups forming small warlord like states in the various ports of the Caribbean. Place such as Florida or Louisiane would be prime areas. In both places, you can shift in and out of small inlets and bays are a dime a dozen in both areas. Going in and out and catching these privateers would be near impossible, especially when there is large numbers of natives to help them hide. Sort of like imagining the Caribbean and Gulf world with a population similar to otl Mexico.
The Caribs - if they still have the same antagonistic relationship with the Taino and presumably the Caribbean-based Maya, might be willing to join the English and French privateers if it means having a technological edge against their enemies.
Now I wonder, in a world where Spain's potential Caribbean holdings are never consolidated before privateers arrive, and faced with native sailors bringing back arms, charts, and allies, if they'll ever come to dominate the Americas to anywhere near the same degree of OTL (if at all).
Mesoamerica, and much of the surrounding areas, would have densely populated, maritime societies with a wider use of metallurgy even after disease takes it's toll (they'll heavily out number nearly every foreigner in the Americas for more than a century at least). With pirate bases in Louisiana, Florida, and the Lesser Antilles frustrating efforts to control the mainland (Louisiana particularly, would strike right at anyone trying to press into central Mexico) and the natives either learning fast or having a ready supply of European allies, anyone trying to control the rim is going to have to cut some major deals. The indigenous polities will have much more weight, not to mention possible "pirate kingdoms" founded by adventurers and escapees. One power may never be able to establish something like the Viceroyalty of New Spain or Peru.
The last Maya kingdom didn't fall until 1697 OTL. Now add the caveat that the Maya are well versed in seamanship. We have the Haida of OTL to see what the potential results could be. They managed to capture several ships and even equip their canoes with swivel-guns. The Maya will be using stronger boats right off the bat and there would be many times more people to boot. This isn't even taking into account the Gulf-Caribbean peoples, who (even with the very first proposed timeline synthesized by
@Skallagrim) would match the Haida in capability. The Maya would have a major reputation as pirates in such a TL (heck a Maya term could be coined for their specific brand of piracy).
With Middle America divided along completely different lines, and armed native polities/rebels, the relationship between all the peoples involved in the region will diverge heavily from anything we've seen in OTL. If one European power does happen to bring all of Mesoamerica into their fold in spite of this it could look more like a "Mesoamerican Raj" than a "New Spain." An amalgam of societies with princely state status given to indigenous kingdoms, quilombos, palenques, and the local equivalent of the "Civilized Tribes."
Furthermore, the difficulty of solidifying the Caribbean and it's shore could have some interesting affects on the Andes. With no one allowing the other to stay too long at Panama, attacking the central mountain polities would prove very arduous. Once more riches are known to be found nobody will want the other to have them all. A possible solution/partition could, by sheer chance, leave an Andean "Ethiopia."
So colonization of the Caribbean may happen if the Mayans have reason to cross it.
One factor I have not really seen brought up is plant domestication. There is a particular species of holly that grows in the subtropical Southern US with the unfortunate name
Ilex Vomitoria or Yaupon Holly. It is so called, because southern natives used it in a ceremony where they would consume massive amounts of "tea" made from it and get hopped up on the caffeine it produces. Basically, it's a North American version of
mate (also a member of the holly family).
Some small changes in genetics and cultural usage could make it a competitor to regular coffee and tea in a wider TL, and would give a handy trade good for Caribbean sailors to cross the sea for. This might drive colonization of Cuba and even further afield; its natural range is the green zone in Wikipedia but it CAN be grown somewhat further south (I researched this once for a planned TL that may or may not ever get written).
With a product worth sailing for, the larger Caribbean islands could be settled by Mayans planters growing yaupon in the highlands... we could likely see some Mayan and MesoAmerican settlement, if only in the form of "foreign quarters", in the mouths of the major *Southern US rivers.
I really like this idea. Caffeinated tea would definitely motivate some Mesoamerican voyagers. It might even help draw in the Gulf Coast slightly earlier, especially if trading the tea without sails leads Mesoamerica and the Caribbean to rely on their imports from Florida, which would have the best of both worlds climate wise.
