The area they have shown had like 80mph winds. I'd imagine Pirates cove all way over to near Key Largo had it pretty bad, but nothing like Virgin Islands. Key had quite a bit of wind/surge but most of that shit is built for it from the pictures I've seen so far. Only the camper/trailer hoods and boats and stuff had it bad. Sadly lots of people didn't leave those areas it seems, we'll see how many. Doesn't do any good to have a strong structure if water washes you away from inside it.
As for imaging I am assuming so. They did a large swath down the coast in addition to the section of keys. I honestly think they already have it but waiting until they have checked the area, cleaned the roads and have things under control before they show the damaged areas to not cause people to panic anymore than they are. Fights are breaking out between enforcement and people wanting to go back and being prevented from entering the keys currently.