I've only done "private" flotillas of various sizes with boats from several different companies. So can't comment except observations on = Sunsail Flotilla. I'm also a repeat Sunsail bareboat customer = disclosure.
After crossing wakes with Sunsail Flotillas, they appear to have their act together, Leaders seem enthusiastic and full of energy + lots of smiles. Customers seemed pleased.
You mentioned itinerary - they give you the option to wander during the day to wherever you want but like to keep track of everyone at the next anchorage. What seemed to missing or was the rub?
The best part about it is for the support @ arrival, pre-departure & during the sail. They will make darn sure everything gets taken care of and provide the "baby step" you are looking for. I would not hesitate to use them at all.
What time of year are you looking at?