I've never heard of that Active Captian website before, but it looks like a great reference tool. I was impressed with all of the details on each marina and anchorage along the way.
The schedule will be the hard part but these fronts are usually pretty predictable. Question(Will I get NOAA wx info on the VHF at Ft. Jefferson?)
I think I need to come up with Plan B and C. If the weather turns sour(cold front) I might just end up drinking at Cabbage Key. Another option might be to make Marco, explore the Little Shark River. Ideally I'd be able to make it to Ft. Jefferson and back to somewhere cheaper than Key West to tie the boat up in time to get back to work.
I think April might be the best bet weather wise.