Yale is much cheaper, is P/F all 4 years, and is much closer to home. Honestly seems like an easy choice to me. Prestige is equivalent. East Coasters will be more impressed with Yale, West Coasters will be more impressed with Stanford, residency directors will likely view them both within a group of 10-15 schools that have very high prestige. USNWR does not determine how prestige is perceived within medicine, you won't get any brownie points for going to one school over the other.
Unless you wanna match on the West Coast and money isn't an issue, it seems like Stanford doesn't really have many pros other than the weather. If you're hardworking enough to get into Yale and Stanford, you're hardworking enough to do just fine with the Yale system. Besides, it'd allow you much more time and flexibility to pursue your business interests.