House Flipper

To get this achievement, you need to own a horse, and you need to have a cavaletti obstacle put down in your residence. You need to mount your horse (first by interacting with it, and then selecting 'Mount', and then you need to ride your horse, and as you come up to the obstacle whilst riding, press X to have the horse jump over it. This may take a couple of attempts, but you'll get the achievement after a successful jump.