1. That's a little tight for making the 230 ferry. go for the later one and your trip will be less stressful
2. You will have no trouble finding first come mooring balls this time of year. Most places will come 'round to collect. You may get lucky and get a free night or two. You can still use them even if the proprietor is not around to collect.
3, 4, 5 - Yeah, lots of places are closed during off-season. There were some other posts on TTOL recently listing closed and open businesses and restaurants. Search for posts by Jason, Ratsman or Manpot.

(Check the hurricane forecast before you leave home)