First off, the island is not that big and you can get from one end to the other driving in about an hour and a half most days. There is good diving on both the east and west ends on the south side. We live in Jan Sofat which is near Spanish Water, Caracasbaai, Tugboat and Directors Bay. I don’t know what your housing expectations are but there is a broad range of home prices in various neighborhoods. If you don’t mind some driving you can get to just about any dive spot within an hour. let me know if you have specific questions. I am happy to help. As for health insurance, we are pensionados and have SVB which is the local provider. It has been better than anything we have experienced in the US (it is easy if your a US citizen). We chose a gated community for the privacy and the ability to stroll the neighborhood without traffic and stray dogs.