Leaving Orlando I would pay it. I did for myself, but I'm the only one flying and $10 on top of a peak airfare just means I won't be having a cocktail either flying down of flying home.
The last 2 times I flew out of Orlando, family boarding was only kids 2 and under.
So with a 3 year old, you wouldn't get in with family boarding. It doesn't have to always be families with kids five and under.
Also, the last time I flew the same flight I'm flying in 5 weeks. I checked in less than 20 minutes after the 24 hour mark. Still I ended up with B's.
For my 7 am flight out on a Monday morning, I didn't bother with the EBCI. I somehow doubt that flight's going to be super full. Plus, I'll just get up at 7, and do the check-in from home as I make my first cup of coffee for the morning.