Your plan will work fine...
...assuming you have a good understanding of and also reliable sources of weather f'cast products while offshore, and you use current GS info.Your Kings Cruiser is a strong, seaworthy boat, so what matters is your navigation & seamanship skills, plus current wx and GS data. The frontal systems that sweep thru and disrupt the prevailing E/SE winds along FL's east coast in the winter are easily monitored, well understood, and you have multiple wx f'cast products available to you while at sea...assuming you have one or more ways to obtain them (VHF closer to shore; wx fax, Navtex, SSB marine & ham wx nets and more, when farther out). So...Q #1 is 'What are your receiving capabilities aboard your boat?' and Q #2 is 'How comfortable are you in your skills to download and utilize the info you receive?'For Gulf Stream conditions, Jennifer Clark is considered one highly-professional f'cast service and you might want to consider purchasing a GS f'cast from her since it will allow you to shape your course to a) capture the favorable current while avoiding eddy's and also allow you to b) stay relatively close to the W wall, allowing you to depart the stream and use one of the all-weather inlets when or if a front is approaching your area while you're on passage.Which leads me to mention I think you've got the wrong idea about 'escaping' to the E if bad weather arrives. A better strategy IMO is to stay on the W side of the GS & plan a W'ly departure in order to tuck in somewhere. Even if you avoid the effects of the N'ly winds on the N'ly flowing GS, you'd still face headwinds (in February, most likely strong ones for a period of time), which wouldn't make sense in your small boat on a N/NE run.These frontal systems may be predictable but they can also be strong, and the days are still relatively short and nights quite long...so don't lose sight of that when planning your run. Offshore temps can also be quite frigid, despite you being in 'southerly waters'. Also, remember that the speed of advance of a front can change, and so NOAA's f'cast of wind shifts and strengths can be somewhat off. I think it's for these reasons that Stu is giving you his cautionary warning.Finally, you might want to do some 'dry run' route planning. ID the all-weather inlets along your route, how far apart they are, and what your longest period of exposure would likely be as you transit N, leaving access to one inlet while still a distance from the next one. That will help you develop a series of 'Go-No Go' decision points and the time periods when stable, non-frontal wx will need to exist for each 'Go' decision.Jack