The later in the year, the less chance of hurricanes. I have been in mid to late Oct and it has been decent, one year we hit in between two milder storms. Some flooding and some heavy rain but nothing too major. Another thing to consider this year is the coronavirus situation and how it may impact travel to and from the US and the island. Consider the length of the trip, the possibility of quarantine both on the island and returning home in your decision as well. Again, the later in the year, the better chance the trip happens.

I am personally looking at mid-November. At this point, there is no assurance it will happen but I am hopeful. Only time will tell.

Something else to consider, most airlines have drastically changed/relaxed their cancellation and change policy due to the unknowns of the coronavirus situation. Most require booking by May 31 so if you are contemplating a trip this fall, you have the added benefit of the ability to change your ticket without a fee or penalty. Check with your particular carrier, the information should be in their websites and most send out regular emails if you are a loyalty member, as to their regulations. If you book and a hurricane looks to be on the horizon, you can use this change/cancellation policy to your advantage.

I can't help with the accommodation availability part of your question but I am thinking thee should be a lot of lodging available once tourism is opend back up.

Good luck.