I used to go to Santo Domingo all the time
1. I would avoid it, you will be putting an extra target on your back.
2. Santo Domingo isn’t really a masseur kind of country but I would recommend Juan Bin Bin (google Juan Bin Bin Santo Domingo), but it’s more of a brothel. I’ve met some great guys there, but before going to DR please expect to see mostly black guys who are a bit ghetto (an understatement) but very hung. Also please don’t expect this to be like Brazil, very different country.
3. Don’t know what to say here, the thing is that the Dominican Republic is full of hustlers do research here, people will try to get you anyways especially if you are white or an obvious foreigner. It’s a very poor country and everyone wants to make money. I suggest that you contact Adam suites hotel and see if the owner Gilber would be willing to do tours. He’s a Cuban American who owns the only gay property in the DR and he does tours for money for his guests. If you contact him he might be willing to do a tour for money even if you aren’t staying there.
4. Yes in the DR it’s okay to wear a speedo to the beach.
5. I think you should evaluate why you want to go. If you are going for purely sex I’d say stick with Santo Domingo if you are going for purely and to relax and have a good time in a resort I’d say yes to Punta Cana. Sadly the gay scene is non existent in Punta Cana unless you spark a deal with a hotel employee (which is rare) and if you stay in Santo Domingo you can kiss luxury goodbye lol
6. I barely speak Spanish and I’m always fine in Santo Domingo. But why the Caribbean? And you don’t have many other options other than Puerto Rico which is having issues now. The rest of the Caribbean are mainly homophobic countries and in some like Jamaica homosexual activity is illegal.
I’d suggest you try mexico in North America or anywhere in South America if you’re looking for Latinos in particular. The Caribbean is very religious and strict with gay laws with the exception of Dominican Republic, Puerto Rico and Haiti.