Yes. You can Uber to the island and it is relatively inexpensive. HOWEVER YOU WILL NOT BE ABLE TO UBER OFF THE ISLAND. Don't try it!!!! We recommend renting a car, or arranging a taxi service if you intend to leave the island. Taxis typically run in the range of $100-$150 to go from Kiawah to the airport.
Yes - Shawn's lovely mother recommends using perfectlypoppins.net for all of your newborn to 12 year old childcare needs.
There are a few restaurants that are connected to each golf course. There is also a little store in the middle of the island, we included the location in the things to do portion of the website. Additionally, there are stores, ice cream shops, and restaurants at the start of the island in fresh field village. We recommend having a car for the journey.
Beaches are free to everyone on Kiawah - find one of the many boardwalks spread across the island and hop right on. The beaches on Kiawah are incredible for biking/running - if you'd like to get a little movement in we would recommend it.
We are working on this with the guards at the gates to share a guest list for the wedding. However, if you share you are a "renter" at your property you are staying at you will be let on the island. All they will need is confirmation of your rental - make sure you align with the place you are staying that they have your information too as the front gate will need this. If you have a rental car, you will be able to get a pass - keep this on your vehicle dash at all times. This will provide you access around the island. If anyone gives you any trouble getting through the gate, just say you are grabbing a cocktail at the Ryder Cup Bar.
That one's a surprise.