Trumps problem is that his strong stance is popular with his base, while a more subtle and refined approach is more popular with those outside his base.
He has secured his base, he doesn't need to reinforce this, they will vote for him in droves. He needs to expand.
He knows the Establishment and people who have been wrong about everything for 30 years own MSM, so he has to be more calculating in these endeavours.
The Trump of the 1980s would have run circles around them with his calm demeanour and logical arguments. If he wants to connect emotionally with those outside his base, do so with pocket book issues. The "Trump cash vs Harris cash" was a good approach. Black jobs are basically any job in their community they might do but can no longer do because an illegal citizen is doing it at half the rate. It's that simple.
These illegal immigrants are horrible for unions as well so any labour union coming out for Harris is suspect and I would look into their leaders finances. Any union member in a labour position knows what mass illegal immigration does to their wages.
The Dems raised the race issue though Trump just echoed the convenient and historical shift Harris has taken with how she identifies. It wasn't Trump questioning her race, it was Trump questioning her and the MSM motives for injecting race into the election. He just isn't as sharp in his method as he once was. His thinking is the same, his use of words isn't.