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Best place to buy a vacation property I can also rent out...with a twist

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I am looking to buy a property that I can rent out when I'm not there.

The twist is my sister's family are also looking and would also like the same thing.

As we will be usually traveling there at the same time (and they have a large family) we are both looking for our own places, close to one another.

Looking for a nice place, for the best value, that can also easily rent out when we are not there.

Thinking of Dominican Republic, Barbados, Costa Rica, Turks and Caicos, or Aruba.

Does anyone have any experience with this?

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