I honestly think he bit off more than he can chew.
Considering that the H.R.'s bill is in line with what the Republican Senate had wanted... aka bipartisan agreement... I don't see Pelosi and her crowd backing down. If they do, I think Trump will absolutely win in 2020.
On the other hand, Trump at this point has everything to loose... if he caves he will be a lame duck... maybe a crippled duck. If he doesn't cave in, he's going to have to convince the Senate to take up his cause, BIG TIME.
He should have taken a page from RR... negotiate for a portion of what you want, then come back later for the rest.