I need 4 advil and a drink

I have been on the net all morning tryna plan a trip. Me and the boy are venturing out in November..and man, is this shit stressful.

From airfare. to car rental. to the skatepark. to the hotel. to the cruise ship. to airfare again.
Each one needing to be a precise time, as to not miss the boat..or plane!

Wondering..should I reserve everything NOW, or wait till September. or October?
should I skip the car rental and take a cab?
Should we stay the night in Orlando, or Tampa?
How will I get to the port after dropping the rental car off?
Will we be late?

I can not fathom sitting in an airport for 7 hours waiting for our return flight..especially with the boy and a bunch of luggage. He (or me for that matter) is just not that patient. That's a long ass time to be sittin in the airport.

I am not a traveler. Travel=stress.

Any suggestions?