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Chicago to Kingston - Oct 2016 (Jamaica)

Hello people!

I head one of the BPOs in Jamaica, albeit I've been visiting Kingston for the last four years every month and not new to the area, I'm at a point of relocating with my family from Chicago to Kingston. This is a whole new ordeal. I moved to Chicago in Protected content India), married to my wife, Riah in Protected content , had a beautiful daughter, Sasha in Protected content . We enjoyed our life in Chicago, now looking forward to three years in Kingston, Jamaica. Maybe in Protected content might move back to Florida or Dallas.

We are working with Allison for find a nice place to live (3 bed townhome/apt), however ...

1) still tossing between Hillel or AISK for my 4 year old daughter, Sasha.
2) Need to buy an SUV for the family, May be a pre-owned Q5 or land rover (budget < 5M JMD). Our office driver has suggested that I buy it from Japan, not sure what's the best to do.
3) We are fun family, enjoy traveling and having fun as a family, and also as a couple.

any comments/suggestions are deeply appreciated.