Jason,
I don't know your plans in detail for your April ride, but the SS1k to your mothers sounds good.
I say scrap the BB, spend time with mom and time your ride to Key West to hit sunrise and or sunset on your ride up and or down.
I hope you are not starting your BBG out of KW.
You would lose an hour off BBG pace by the end of your first tank. I have a guesthouse right off of I-95 you are welcome to stay in. I could set you up with witnesses and for your first BBG, you will want some type of tracker for others to enjoy your ride. If you don't have one, you can use my spot.
By adjusting your route with "Corners", you can plan a BBG route back home with faster areas than KW, keeping the 2 hour padding for traffic or a roadside nap.
I am working now, but will send you a PM with additional info. I ran a BBG from WPB to your area 2 years ago.. The trip in the fall... That would be great!