The problem is Congress has to send him the legislation that does what he wants. Otherwise there's very limited stuff he can do by EO.
As much as we complain Obama's executive amnesty is still being blocked by the courts. Trump won't fare any better.
Obama had the entire Democratic party fully behind him. Don't forget, whatever happens with Trump the congressional situation won't be radically different after the election and he's going out of his way to alienate the establishment types that will still control the Republican caucus. Again, I'm not sure he's cut out for this whole co-equal thing.
As a winning president who ran on a ‘signature’ issue he- like anyone else who did that- would have the needed support.
That’s just politics.
Most of his immigration reform is what is already law. The congress hasn’t funded it!
That is the legal rationale Obama used for his amnesty: he hasn’t the money to enforce the laws hence he’s justified in using prosecutorial discretion.
Of course every issue can’t be a signature issue. On immigration, though, he can deliver.