You have put into words all my concerns on Trump, mainly that I worry he might resort to EO’s to have success, but that in the long run, it damages the constitutional fabric. I have no problem with the use of EO’s to “undo” anything that the current or past occupants have wrongly done, but I think that new-slate governing should emphasize constitutional strictures.
I don't think Trump should hold back on EO's. I think he should go all out on EO's which roll back every gain the Left has made in the last 40 years.
THEN, he should sponsor a Constitutional amendment to permanently gut the power of EO's to do things that should have been done by legislation, and the power of the Executive bureaucracy to legislate via rule-making, and judge their own rules in "administrative courts". And tell the Dems if they don't support the Amendment, he's going to keep going on the EO's until the amendment passes.