One of the biggest problems IMO is finding the day an airline flies non-stop. I usually book the hotel before the airline and often find the day I booked AA one year ,non-stop, is not the same the next year. I then try to rebook the hotel hoping that the non-stop day doesn't change again or disappear.

I just checked Delta for November and found that they only fly JFK to SXM, non-stop, on Mondays and Wednesdays. I am going on a Tuesday and don't want to change the hotel again.
There are also certain days they don't fly to SXM, which makes me nervous about a cancellation due to mechanics or weather.
It's all a gamble..... <img src="" alt="" />