Yeah, but what if the MC also makes a trust and a will where he points that in the case of his untimely death all of his assets (present and future) have go to Katie or Monica ? He wouldn't be breaching his conditions, they would be met some 10 years later and his part of the money should go to whoever he picked, right?
Also i think Elaine is trying to find out which animal shelter the money would go to if all fail their conditions, so she (or Bella) can buy it and the money go to them in the end. Seems like screwing everyone over is much much easier than completing one's own conditions.