Hi, and thank you for the invite, zwiebel. OK, so you ask about the places in the Caribbean that a Dutch born person with multilingual skills/US residency would feel most at home.
As you may be aware, there were two groups of islands in the Caribbean which used to be under Dutch Control, but now, not all of them are. Together, they formed an autonomous country. There were a majority of Dutch speakers on these islands, Aruba, Bonaire and Curaçao (the ABC group) and Sint Maarten, Saba and Sint Eustatius (the SSS group) - combined, they were known as the Netherlands Antilles/Nederlandse Antillen.
Aruba is now independent, Curaçao and Sint Maarten are constituent countries of the Netherlands, and the rest of the islands are special overseas municipalities of the Kingdom of the Netherlands.
As for which places would be most likely to feel at home for the subject, your likeliest target would be Sint Maarten, which is *in the US Virgin Islands, and (being a constituent country of the Netherlands) would fall under their extradition treaty with the US (ratified by Sint Maarten in October 2010). Unlike most extradition treaties, anything between the Netherlands and the rest of the world (where treaties exist) is generally pretty swift, taking no more than 6 months to a year at most.
The other place with a possibility of a target would be the Bonaire special municipality - it depends on their multilingual skills, but Bonaire has 3 languages in daily use, Dutch, Papiamentu and English. It's also a pretty nice place to hang if you are trying to stay under the radar.
