cheapest: Bahamas, DR, TC, in that order....with TC trailing so far behind the other two it gets lapped twice.
easiest (for non-Spanish speakers): Bahamas, TC, DR (I'm assuming Puerto Plata here when I say DR).
In the end it all comes down to range. You need an honest 600NM range with IFR reserves when going east in order to bypass TC. My Arrow II doesn't have the IFR range for a DR to FL, or Bahamas to PR leg. I can do Great Inagua, but their avgas availability is all over the place and they're cash only, plus getting stuck AOG in Inagua is not my idea of a leisure trip. For those of us with short tanks, TC becomes a necessity if one intends to do the crossing without incurring a third leg (which incurs ATC overflight fees for the intl to intl legs). Which is why I won't do that bucket list trip until I have a longer legged airplane. Most people with 4 bangers and at least 60 gallons usable should be fine bypassing.