Silver Air - we landed in every major Florida airport on the way down and back (Pensacola, Tampa, Key West, Fort Lauderdale, Orlando) which was a pain but every flight was on time and everyone was friendly. Only downside was it must have been 90 degrees in those planes. AC was non existent.
Southernmost Hotel - nice room, friendly employees, fun pool with great bar. The beach was pretty bad but that was to be expected. Smelled like sewage, seaweed everywhere and water was dingy. We spent most of our days hanging out at the hotel pool and talking with the other guests. The bartenders were great.
Sloppy Joes was awesome once the band started. The two guys who came on early in the night were terrible but once they left it improved greatly. Everyone was having fun and drinks were easy to get. I highly suggest this bar.
Green Parrot was a big disappointment for a Friday night. It was dark and no one was inside. Totally dead.
Blue Heaven was the best meal we had. The egg benedict with local sausage was great. We ate inside then sat in the courtyard, drank and listened to the band. What a cool place to hang out.
Pepe's was delicious and service was excellent
Camilles was disappointing - ordered the crab cake benedict and it was too sour and just not good. Blue Heaven's was 100x better. The service was great and friendly though.
Schooner Wharf Bar was ok. Good bushwhackers but we weren't impressed with the place. I can see it eventually being torn down to fit with the other improvements to the area (I know this is a sore subject but it's bound to happen)
One thing we noticed was that the Thursday and Friday nightlife crowds were much more enjoyable than the Saturday night crowd. Saturday night was packed, we saw several fights and the crowd seemed a lot sketchier. I'm sure this is the case almost everywhere you go but you may want to keep that in mind when you plan your trip.
That's about it. Thanks to everyone for your help.