An excellent idea!
May I humbly suggest a 5 to 10 mile race so that the more casual runners can participate. Although Bay to Breakers would be great, anything more than 10K participants could be difficult from an in-race logistic standpoint (starting and staying together, as well as finding people at the finish).
Usually early February is the Gasparilla 15K in TPA and the Gate River Run 15K is in JAX on the second Saturday in March. Both have about 8,000 runners. Since we spend so much time in the air, is there a 10K/15K near the House of Miles?
Started 5 Bostons- only finished 4. That darned broken leg wouldn't go more than 17 miles.