He doesn't like driving the element, the older prii will open up to carry most anything, the prii will get double the gas mileage, be a two prii family, all the way to the gas pump
Does your Element have the 3.5 liter V6 motor? Those motors need a new cam belt at 100k miles and it is not cheep to get it replaced Mike Mobile on my SGH-i717
If you can afford it I would keep both and add the 2 Prius to the fleet. Keep the Honda for the dirty work and use the Pri to save money as daily drivers. I am kinda surprised that you have had issues with the Honda. Brake problems???? Are you sure you don't have mechanic problems?
IIRC, all Elements came with the 4 cylinder engine. From my test drives, it was fine around town but felt a bit strained on the freeway.