I feel very safe living on the Big Island, but plan to move to Davao City Phillipines if my wife predeceases me.  I would have moved already if not for her health problems.  Davao City has a Safety Index of 71(higher is better), Honolulu is 52.93, only moderately safe.  Davao crime index is only 29 (lower is better), Honolulu is 47.  In fact, Davao is one of the safest cities in the world and 80% speak fluent English.  All court proceedings are conducted in English and they have world class medical facilities with doctors and staff fluent in English.  You can rent a luxury 2bd/2ba air cond condo next to a large mall with dozens of restaurants, very large grocery stores carrying many imported goods, have a full time live in housekeeper/cook and eat all your meals out including Western fine dining if you wanted to for $2500 a month.  That level of income will put you in the top 1% of wage earners.

how do you pay for medical expenses there?

I feel very safe living on the Big Island, but plan to move to Davao City Phillipines if my wife predeceases me.  I would have moved already if not for her health problems.  Davao City has a Safety Index of 71(higher is better), Honolulu is 52.93, only moderately safe.  Davao crime index is only 29 (lower is better), Honolulu is 47.  In fact, Davao is one of the safest cities in the world and 80% speak fluent English.  All court proceedings are conducted in English and they have world class medical facilities with doctors and staff fluent in English.  You can rent a luxury 2bd/2ba air cond condo next to a large mall with dozens of restaurants, very large grocery stores carrying many imported goods, have a full time live in housekeeper/cook and eat all your meals out including Western fine dining if you wanted to for $2500 a month.  That level of income will put you in the top 1% of wage earners.

how do you pay for medical expenses there?

Since I am over 65, I cannot get medical insurance and Medicare does not extend overseas.  Most expats pay out of pocket but because it is so cheap, almost all doctor visits will run between $9 to 26USD.  A complicated tooth extraction will run $52.  An appendectomy at a teaching hospital $350 or $1750 at a private hospital.  Simple bone facture of the leg is $435 or a complicated compound facture requiring bracing and screws can run up to $6100, compared to US rates of up to $50,000.  I have done close to 20 hours of research about where to move out of country and still researching.  This is something I will do if my wife predeceases me.  My classmate moved to Thailand years ago and is happy there, but the language barrier is a big negative.   

Another reason I picked Davao.  It is outside of the typhoon and seasonal monsoon area.  It does not get days of heavy rain during the monsoon season like Manila.  Since 1970, Davao has had only 2 typhoons hit the area.