>Ideally each team would be 3-4 people. <

A side thought.
How about increasing the size of the team?
Say Team Fort Walton, Team Pensacola, Team Miami, Team Tampa, Team Aus, Team Euro, etc.
Say each member of the team member sails 200 miles(or two legs) of a thousand or two thousand miles.

With a huge team you could sail from Corpus Christi to Key West.
Team size: 2000 / 200 = 10 crews x 2 members per crew = 20 team sailors + Land crew/managers
With a larger team individual members time/cost would be lowered.
Team practice would make their team faster than others.
You could position the team members based on skill level vs leg/wind difficulty.

Whose town wants the bragging rights?
Team spirit and quantity of spirits consumed would be dramatically increased, etc.
Finish line party would be hug mon gus?