The dollar can be used once a day. It has to be a dollar’s worth of a product, service or use of a product. For example, A dollar’s worth of a $100 TV would be the life of the TV divided by 100. You would get to enjoy the TV for that amount of time. The product or service is instant and doesn’t require any preparation. It just appears and disappears. Or you could have a TV permanently that is worth one dollar.
Twist: you keep the velocity you gained during the drop and splash on the living room floor right in front of your family.
Ballpark $300 per go, typically ~10,000 ft, internet says that’s 30 seconds of freefall… I think you can get a dollar’s worth of skydiving by rolling out of bed the wrong way.