Booking DCL Sept 2027 tips please.

So thanks to you all, we already put a dep on a 5 night Fantasy for the 3 of us (daughter will be 4 yrs old). We wanted a 4 night but 5 was the only way to get both islands, with Nassau being first. 9/5/27; floor 9, 2 below the pools, like recommended (8 was slightly cheaper); interior like I wanted but only a couple doors from my group's balcony room for 5, a short walk, across from elevators. It was roughly $3700, which I have sticker shock even with expensive expectations, since this doesn't include flights. 1st dinner. I think there is a pirate day with optional dress up.

We're leaning towards buying the insurance, roughly $200, not just because of hurricane season, but if someone gets sick/hurt. What do you guys think on that?
Any reason not to prepay gratuity?
If we do stick with a WDW stay beforehand, and buy a Mears Connect bus from MCO to motel. Is it best to Uber from resort to port or use a shuttle?
Does it make sense to get a later Port apmt. like close to 3pm, to try to go to MK until like 11/12pm? With the 5 night, we'd only be looking at a 1 or 2 night stay so potentially only 2 park days without anything on the Port day (and first day being a partial flight day).
 

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