4 Square, we lived in Tampa and often went to the "other side". Channel 5 is tall enough for your boat, but its a pain to bob and weave through Florida Bay. Last time I did it in 4' draft boat quite some time ago and had some challenges.
Key West is way out of your way and the Hawk Channel is a pain to negotiate in many wind conditions.
However, the 7 mile Bridge is 65' clear and has an excellent harbor at Boot Key. You can anchor
on the south side of Boot Key harbor "outside" if you wish and dingy into the harbor for various services. There is a West Marine, good food market, etc, etc.
I carried 6' draft from Tampa to 7 mile bridge with no problems, though you do have to watch very carefully just north of the bridge--say for the 10 or 20 miles north of the bridge.
On lobster pots--during the season they are a major hazard. We carried two of them into Boot Key one year, caught on our rudder! The pot lines
were jammed between rudder and skeg and we dragged them the last couple miles into the harbor. In fact, on TWO trips there, we caught lobster pots. However, the season ends shortly--I believe May 15. And it doesn't start until I believe August 1 (you might check those dates). The sport lobster season begins before the commercial one--its the commercial start that puts all the pots out there. So if you can do the delivery between May and July, you will not see many lobster pots.
The gulf stream is a bear when you get a north wind against the north-flowing stream. So many boats wait for weather in Boot Key. I personally would not try to do the inside route from Boot Key to Miami in anything over 4' draft.
We have done several deliveries from Tampa to the north--Chesapeake bay, etc--and you might want to consider this path.