Seriously, pin him down and ask him to explain in detail how he proposes to pay for his promises. This BS of taxing the uber rich won't pay for it. Then ask him how he plans to reduce the deficit and watch for the infamous deer in headlight look
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If you bothered to read his website he has his positions and explanation of how to pay for the stuff there.
He would open Medicare to everyone and then they would pay Medicare premiums like I do and with everyone paying Medicare premiums there would be plenty of money because that system is not based on making a profit and doesn't have multi-million executives running it. There are no million dollar bonuses for tricky language to get out of paying. And no BILLION dollar profits which makes the money go much further.
As for free college he wants a tax on each Wall Street financial transaction. Like $1 per trade. There are literally billions of trades each day. Would not be a tremendous burden on stock holders / traders. They are playing with thousands of dollar or more on each trade. $1 would not even be noticed but would produce tremendous amounts to finance the free educations.
BTW For Porfit Insurance companies could still sell Medicare supplement policies as they do now but not Medicare Advantage. But they would not be out of business entirely ( unfortunately ).
You do realize that insurance companies are socialist in their very nature. With a profit added on top for organizing and collecting and paying out to those policy holders who had medical issues.