[djokkataja]

Do the BSc + premed and evaluate the medical thing more deeply in your third year--or graduate, work for a couple years, and then decide. Work can provide a lot of perspective that's difficult to get otherwise (assuming you're still in high school). It's tough to plan your life that far in advance; you might develop more specific interests as time goes on (plus expectations of what the industry will look like may change over the next few years too). Even if your plans change considerably, EE + premed is a solid background, so transitioning to a different field wouldn't be a huge pain.

1. Automation will have a big impact on medicine, but it will be an ongoing process, not something that happens overnight. If you're doing a joint MD/PhD(EE) program, then you'll presumably at least have some technical qualifications that would make you more appealing to a company that is working towards the automation of healthcare.

2. You might be able to start a business on the side, but not as a resident unless residencies become immensely less stressful and time-consuming. Part-time work as an oncologist may be hard to negotiate early in your medical career, but I am not a doctor (though I did investigate similar questions a few years back, and this was the impression I got from speaking with doctors and MD/PhDs). Financial feasibility... as an MD/PhD, you shouldn't have much in the way of personal debt (since the PhD covers the MD tuition as well), and I wouldn't expect you to be dipping too close to the poverty line.

Realistically, it depends a lot on whether you have a specific business idea in mind and what your drive looks like. Those aren't things that you can plan very well 20 years in advance.