What kinda supplies would be helpful? Josie Graves still wants people coming for the winter season, and I'm sure most others feel the same.  

Edit: I've been going every winter for years and I'd feel bad if I didn't try to help out in person this winter

I can't speak for other people, but I know when we lost the roof of our property and didn't have electric for a few weeks, I was more than happy to have a tourist or two to spend money in our town and hopefully stay at our place. Of course we weren't really roughing it in comparison to PR. (To be honest, I was more annoyed about people acting as if FL had fallen into the ocean.)

Not everyones going to see it the same way, but I guess if you're staying with a local, helping out a bit, and spending money while enjoying a few surf sessions with your local Puerto Rican friend;

What's the worst that will happen?

Good supplies to bring to help out? The most basic stuff. Underwear. Those little wall lights you just stick on your wall push it and it turns on. Soaps. Tampons and other feminine hiegiene stuff. Lighters. Candles. Deodorant. Old clothes. Insect repellant, especially for you. It's hard to find water, let alone clean water. It's pitch black at night so stay safe. locals need BATTERIES. I came to Central FLorida when I was 4, but I know my family's situation, even my affluent lawyer cousins in San Juan are having trouble. My cousin just came into the Tampa Area the other day for a Nursing job interview, that should give you an idea. I really wouldn't recomend the trip. Hardly any street signs, if any at all, even without storms, so, paper maps wil be very difficult to use let alone the absence of cell signals for google maps. Many roads are counter intuitive and winding. Generators are cool except for the loud sound they make all night. Take ear plugs for you and the locals, they are having trouble sleeping because of the noise from generators. Hours in line for gas that might run out once you get there. Had a whole bunch of relatives come and tell me much more. Leptospirosis. etc... Ad Nauseum. 

"If the highest aim of a captain were to preserve his ship, he would keep it in port forever."-"Now relaxation of the mind from work consists on playful words or deeds. It becomes a wise and virtuous man to have recourse to such things at times." St. Thomas Aquinas ("The Angelic Doctor")