It's all pure speculation. IMO he's a loose cannon that could do anything, or one thing one day and another the next. He's promised to get rid of all Obama's executive orders, which would include the one opening up travel to Cuba for individuals.
For "more informed" speculation, maybe join the discussion with a bunch of folks who spend a lot of time in Cuba, on the Lonely Planet's Thorn Tree forum. Their speculation is that whatever happens, OFAC will not get sufficiently more funding to show up on your doorstep demanding that proof you're supposed to keep for 5 years.