Yes, fronts would be my primary
weather concern. But if you play them right they can also
work to your advantage by shifting prevailing winds. The ugly
weather will be at the leading edge of the front. You can hole up somewhere for that to pass and then catch the shift on the trailing edge with more stable weather, but maybe some leftover sloppy seas.
Maybe "most" fronts don't push that far south in December, but plenty do, and its typically the stronger ones.
I worked for years in the
charter industry in
Belize and we would get cold fronts pushing down from the
USA from December to as late as March. In 2011 we had fronts thru the entire month of March. The ideal time to transit the GOM is April-May. Its after cold front season and before
hurricane season.
To access the risk you need to get familiar with Pilot
Charts, NOAA Synoptic
charts, and maybe a pro weather router like Chris Parker.