Bloodsworn establish a colony in eastern Cuba and on Jamaica. They also make bases in the great island chains in the Caribbean. They take an interest in a certain crop, seeing thst it would be a useful addition to Ologor's chefs.
You do understand that in this time most of the world is not aware of what are diseases exactly and what make them spread. Except for jews, we used to wash our hands before eating and to take showers while the rest of the world used to put dirt on their skin to keep the diseases away.
I think you (and gamer) should pick colonies last because of the fact that you have to pass first the entire old world. And no, you still think that the world is a giant plate or whatever so you can't make a short cut by just going east
Dirt creates a protective layer, and mosquitos and other biting insects will not bite you. Covering yourself in dirt can save your life in some situations