I haven't had my coffee, so bear with me.
The first thought I had was that if this fellow needs to win the lottery to retire, he cannot afford Punta Cana. Seek elsewhere friend.
That said, with good planning, there are places where you can retire, fairly comfortably with a lot less money than you think.
It might require some inventive life-style changes, but it is certainly doable.
Thing is, the ex-pats you will meet out in Punta Cana (those that are retired and living there) are, generally speaking, fairly well off with stable retirement income.
Next thing is that life out in the East is very limited, blindered if you will, with social interaction among "sets" that revolve around golf and cocktail parties and society, with a few "do-gooders" mixed in.
Finally, you are NOT REALLY in the DR out there. You are in what we call the Independent Republic of the East. The only time you meet real Dominicans (except for your maids and gardeners and other workers you might employ from time to time.) or real things Dominican is when you pass through Veron or Higuey on your way to a concert at Altos de Chavon or on a shopping trip to Santo Domingo.
I would suggest that over the next 8-9 years (unless you win the lottery) you explore other places such as the North Coast and the major cities and the not-so-major cities to see what the place is really like....you'll be surprised at the variety and complexity of the place.
Good luck....go really, really slow about purchasing anything for the next few years--especially in the East, called "the Mecca of forged property titles."
HB