Jeeeeez, I don't get it. A 220lb self-proclaimed boxer AFRAID of getting ripped off in a third world country consisting of 99% GREAT PEOPLE. Dare I mention he's from a major U.S. city too? Puhleeeeze people. Stop with the horror stories and fear. SD is fine, the DR is fine........quit trying to scare the guy.
Yo my Brooklyn Bro, I'm fitty years old, as white as Wonder Bread, although I work out hard everyday....I'm taller than you and I out weigh you....you'll find you will have visual respect.
I don't get overcharged for nothing...just ask before you buy, check your receipts and treat everyone like you're visiting thier house. Be nice. I eat out at restaurants, drink for hours in bars, shop.... usually with a DR cutie with me....I've NEVER gotten a bill that was out of line for the fun I've had.
When you walk/stagger anywhere, know your surroundings, maintain situational awareness and try to have someone with you. (Loners make good targets anywhere in the world) I use a local driver occasionally, and when he's not driving me, I always invite him....he's a good pal.
As far as the clubs go....dude, it's just like home, when you go looking for trouble you'll find it....hit a couple clubs, meet a few "friendlies" and choose them on your gut feeling (jus like the good ol' USA)...FYI-the ladies of the DR are far superior to any in the USA.
I make copies of my passport, driver's license and gun permit (all from the USA)...all photo IDs. When I hit the DR, I staple that paper to a business card for the hotel I'm staying at. I've never been questioned terribly so. Yes I've been stopped by the police...no problems (If something does happen to me-my paperwork will make a good toe-tag)
Carry enough cash to buy what/who you want, pay in pesos, don't be flashy. Wear a money belt, not the ball-sack belts, a 1.5" regular money belt. I always carry mucho dead Presidents in mine. (US$,$$$)
When you leave your room, lock stuff in the safe, hide money in three places in the room so if you get hit, they won't find all of it.
Also, a super-sized Presidente in hand makes great self defense....intact, the bottle is heavy and when landed properly upon an attacker will disuede any further attack.......when shattered, the Presidente has proven to be a grand "cuchio" (knife, gringo)....this has worked for me in Panama, Honduras, Guatamala, Serbia, and Canada...
If you're really nervous, PM me, I'll come down and be your bodyguard, I'm always up for an adventure.....it's how I earn a living