You must make the boat insurance decision based on your own circumstances. Having been caught in Ivan in Grenada and seeing how no insurance (or poor insurance) affected and changed the lives of many, I am a big proponent...and it is not only storms that one has to worry about...other uninsured boaters, running into a reef etc. can be just as individually devastaing. If you decide to insure, may I recommend IMIScorp.net out of Annapolis and their Jackline policy from Markel. They took incredible care of us.
On the medical insurance front...we opted for a very high deductible policy from BC/BS in our home state figuring we were in good health and could handle the "little stuff" at down island prices. Medical prices really are quite lower elsewhere but so is the level of care. Fine for broken bones and cuts but I'd want to get back to the states for anything really serious. Short story:
A friend of ours came down with appendicitis in the Dominican Republic. It took 3 hours to get her to the hospital where she was operated on. Sanitary standards were not up to par and she had a massive infection and had to be flown back to the states for another operation 2 weeks later...very lucky to survive.
The evacuation policies may be of value if finances are tight, but we figured we could handle those ourselves if the need arose. Depending on your existing health and finances you have to make your own decisions. We figured we could handle most anything that came along, but wanted the protection of a high deductible policy in case of cancer or stroke or other long term debillitating and expensive illness. You can get deductibles up to $10k in some places which really lowers the monthly payments.
No longer posting. Reach me by PM!