Lauderdale is going to be tough with boat and trailer. Try American Offshore they might be able to help. Maybe someone else will know more. When I kept my boat in Lauderdale the trailer was sent out of the city for storage. You could always put the boat in a slip at Bahia and go to the bars. This trip is alot of fun. I've done it several times. The keys are tough to beat this time of year.
4. Which route is the best route to take, inside or outside or both? Outside is well marked, inside can be a problem if you aren't familiar. Gps will get you 1/2 way down on the inside without too much worry.
5. Where is a good place to stop in the Keys on a Saturday night? I was thinking Islamorada area. Islamorada is a very good place if you want to make it a 2 day run. Kinda midway, marina and bar, what more could you want?