[Texas Bill]

John;
Your best bet will be as follows:

1) - Document your vessel with the USCG at the time of purchase. Might be better to form a Sub-chapter S corporation and place ownership of the vessel in it's name.
2) - Get some good insurance coverage and keep an up to date inventory of equipment and spares along with original invoices of their purchases. You'll have a lot of stuff stolen and will need these when you file your claim.
3) - During one of your trips to the DR, make the acquaintance of some reliable Dominicans (male and female) who KNOW HOW TO SAIL. Most do not, since they haven't been exposed to that sport. Make sure they possess an up-to-date valid passport and are not considered to be in the ranks of undesirables.
4) - Enter the DR at Manzanillo or Luperon and start your DR journey from there after the Dominicans whom you have selected as crew arrive and you are ready to proceed.
I recommend Luperon since the Commandancia there is accustomed to dealing with onward travellers, it being a major stopping off port for such.
5) - When you finally arrive at the South Coast, you'll be in a position to convert your vessel into a money maker by forming a Dominican Corporation (after getting your temp residency) and conducting day charters for the tourists that frequent the area.

Number 5 may take a while, but will be beneficial as an income supplement to your retirement.

In answer to your ?'s about gunkholing; there are NO good areas for that sport in the DR that I know of. Take a look at the ONLY chart available! The data presented is over 50 years old and really not all that reliable! Also, bear in mind that local fishermen WILL NOT provide you with any local information regarding such. They are very secretive about where they get their livelyhood.
Just a word to the wise.

Feel free to contact me about any other advise that I might be able to offer.

Good Luck!!

Texas Bill