Sumner, I went tru some of your trip around Cayo Costa tru Naples. I could have givin you local Knowledge that could have put both your MacS and the 4.6 to 5ft. draft on your Endeavor 37.
Many places you have missed that you could have entered and are well worth exploring.
Next time you do this give me a call and can meet up at a anchorage, or will tell you about entering a Port South of Boca Granda to Naples.
I am happy you had a good trip and not taken chances without local knowledge.
Currents tru all passages can be 2-3 knots or more and channels do change often, depth also changes.
Some that change are very little is Cayo Costa hugging the Shore Line, Picnic Island (East side). This is for your Endeavor 37.
Your Mac S will go to any anchorage you want.
Even with full load 5 ft. draft there are areas you can anchor in safe harbor along your route.
I enjoyed so far your report and looking forward to reading it thru.
Dave