Was it his support of Democrats up until 2008 and his vote for Obama that got you to like him? Or his conservative rhetoric up until he was the defacto Republican nominee? Or is it his higher taxes, single payer health care talk after he was chosen?
That more or less matches my own dispositions in those timeframes. I remember casting a vote for Obama but only because even back then I was very strongly #NeverHillary and knew nothing about Obama himself. I probably did or would have cast a vote for Obama in the general because the alternative was Crazy Johnny (later known as 'Jihad Johnny'.)
I may have given up on the potential for single-payer to work by that time, but I did support it at one point because it provides the best leverage on a theoretical basis among other more broad benefits. At the time I did not recognize that the health care system was being broken on purpose for nefarious reasons and by those who wanted universal care to further ratchet up their game. By the time Obamacare rolled around I favored a public option specifically to help the right people have leverage in 'making the deals'. States may not be the best allies of 'the people', but they don't print their own money so they have at least some reason to try to control costs.
I believe in 'higher taxes' for groups who have used their influence to insert loopholes into the tax codes and who leverage these loopholes. Always have, and I believe that if Trump is at his core a decent person then he probably would and did as well.
I don't have anything against people who 'flip-flop'. I do it myself. I do have something against those who will not flip-flop even when new information comes in. They either are not exposing themselves to it or are to fossilized (or bought off) to take it in. Generally I find this inflexibility to be the biggest problem with the hard-core Libertarian types.