I believe the penalty for overstaying your six month visa in the Dominican Republic is $28. I have a client who is doing precisely what you propose doing. He is

I believe the penalty for overstaying your six month visa in the Dominican Republic is $28. I have a client who is doing precisely what you propose doing. He is happy. Two small kids, a wife, and decent internet access. He is making a good living. Watch out for your US tax filings though.