Breaking with party orthodoxy on gay & transgender issues is a smart move politically. The tax thing probably is not. Trump will lose more conservatives than he could possibly make up with liberals or moderates.
Not really. The GOP hurts itself way too much by its tax position, and they are often out of step with their base. If anything, i'd suggest the opposite - the trans issue could be riskier than endorsing tax rises.
Correct. If the Trump campaign has proven anything, it's that rank and file Republicans are not Chicago School ideologues.
62% of Republican primary voters have voted for a doctrinaire conservative. Many of those voters will not vote for Donald Trump because he's not conservative enough (in a traditional sense). Trump can not possibly make up the difference by appealing to liberals. The transgender position is smart because it neutralizes a Democratic attack line, not because it's winning over any one.