We have mainly easterly quadrant winds in the Keys. When Dave Calvert and I came up with the race back when, the idea was to race 100 miles to KW. And mainly it would be all a downhill spinnaker sleighride.
Reversing it would make it a tough uphill trek.
Logistics have always been a bit of a problem. Marathon was a red tape problem, Key West had a finish line problem. When it started on the Bayside of the Keys, Upper Keys Sailing Club were very hospitable, and started the races in Buttonwood Sound -- great racing as it was part of the second day of the Steeplechase in reverse.
Personally, I never have cared about starting from Islamorada.

Also, too bad about Hogsbreath changing management. They have also been there to sponsor the Wave Nationals. I suppose that is gone now as well.

Any thoughts on making the race work will most certainly be welcomed by Warren Green, who is trying to keep it together.
Rick