First of all congrats! I think I can help with a few of your questions.

1) The front row of the c/o beach is a bit congested with chairs being closer together. If you don’t mind the 2nd or 3rd row, the chairs are much farther apart. Also, when you get there are find a nice spot for yourselves, just ask one of the beach guys setting up the chairs if they can set you up there. They are very accommodating.

2) There are a couple small c/o inns in Orient Bay. Club Fantastico is one. I can’t comment of them as I have never stayed at any of them. Of course you could rent an Airbnb/VRBO with a private pool and sunbathe as you wish.

3) Walking topless to/from the beach would not be acceptable. It is reserved for the beach or your own private space.

4) Orient Village has some amazing restaurants. My favorites are Maison Mere and Le Piment. Also Grand Case is a short drive away. In GC we love Spiga and Oceans 82.

5) Personally, I wouldn’t spend a lot of time after dark on the beach. However there are some of the beach bars that are open for dinner into the evening a few days a week. That may make it more safe to walk after dark.

6) The Perch is a great bar to hang out at c/o or topless. There are boat excursions as well that are c/o. You’re not going to see topless only, it’s c/o or it’s not. Remember c/o is clothing optional, you have the option to wear any clothing or none at all. Both is acceptable in a c/o setting.

7) I can’t comment of this one. Not an interest of mine.

I will say, if the water shutoff issue is a big concern of yours, confirm with whom you are renting from that they have a cistern. This will eliminate any water shutoffs from disrupting your visit.