I recommend that you go to Puerto Rico instead. There are more boats there, much less regulation, and people pay in dollars
You have at least 2 options: (1) work at a marina or for a marine contractor, (2) go to a busy harbor like Boqueron or Salinas and work as an independent.
I live in the DR so obviously have nothing against being here, but I was a cruising liveaboard for 15 years so have some insight into what opportunities you would have in both places. Puerto Rico is where I would go if in your shoes.
I'll elaborate a little on my reasons for encouraging you to go to Puerto Rico:
1. You mentioned possibly chartering your boat. In the DR, you will need to flag the vessel, which can be quite expensive. And you will need to clear out with the Port Commander every time you leave the harbor.
2. Getting parts, supplies, etc, from the US when necessary is much faster and cheaper in Puerto Rico than in the DR. Also, in the DR if what you import costs more than US$200 you must pay duty. In PR you can use the US postal service, or if you use UPS or FeEx, they charge much less there than here because they are in competition with the US post office.
3. There are more support services
4. In PR you won't have trouble with locals who think you are taking business away from them like you can expect here if you work as an independent and they feel you are stealing there customers.
I spent quite a bit of time in Puerto Rico doing haulouts and shopping trips and used Americans working as independents there for a variety of things, such repairing and rebuilding my alternator, repairing a cracked block, and installing a new antenna on the top of the mast.They were making a good living.