There is always something going wrong in the drilling business. Always breaking stuff, rain, getting stuck, redrilling the same hole. It is hard to give any kind of schedule. The trick is to not give the 50% down until the rig shows up in the yard. Sometimes people get on several list, pay the first one to come, call the rest and cancel. Drillers hate that but it works. Even when he gets to your place it may take a while. If he has to redrill or something else, you don’t want him leaving your place early just to keep a schedule with the next guy. Scheduling anything requiring water before the well is drilled is counting your chickens before they hatch.
As for everyone showing up for the holiday, the same pump system needed for the well can probably be used in a 1,000 or 2,000 gallon plastic tank and have the water hauled in. Then when the well is drilled, you can move the pump to the well. Pain in the butt I know but, some people live that way.