I have exactly the opposite view.
1. Trinidad may have a high crime rate, but it is way safer than
Panama,
Columbia, or
Venezuela. One fellow cruiser got mugged in the stairway of the immigration office in Colon, and the standard procedure is to take a taxi between shops in broad daylight.
2. You need to supervise or have supervised any boatwork if you want good results, whether it is in
Miami or Trinidad or
Panama.
3. The spoken language in Trinidad is
English. You can communicate easily and directly with workers, managers, and bureaucrats. Not so further west.
4. Trinidad has a
customs office in Peakes yard, where you can pick up courier shipments duty free and (mostly) hassle free. Not so in
Grenada or further west.
5. Trinidad has way more
boat infrastructure than the other places. Big, well maintained travelifts. You will have your choice of welders,
wood and
fiberglass workers. Good Mechanics and
electrical workers are harder to find.There is a boaters office with a book which lists all the workers.
6. If you have any questions in Chagaramas, they will be answered on the morning
VHF radio net.
7. Trinidad has Carnival, with spectacular costumes and great
music. You can watch, or better yet participate.
8. Trinidad has Jesse James, a tireless ambassador to the yachties, who organizes tours to Carnival and the many other attractions. If you get sick, Jessie will take you to the right hospital, etc.
9. I don't remember a
single boat being hit by
lightning in Chagaramas, but if your boat spends
hurricane season in Panama it has a significant (15%?) chance of being damaged.
10. Both Peakes and Powerboats have pretty good
security, and at least Peakes has a fenced within the fence to store layed up
boats.
11. If you leave the boat in Trinidad, it is easy to spend another season in the Windwards. Once you go downwind, you aren't coming back.