The point to which he was getting at was in comparison to how you live how do you think people along the border feel about people trespassing across their land to gain entry into the US. In regards to that you felt the wall was a waste of money, doesn't deter the reason why some are crossing and doesn't deal with the issue of visa overstays. That's called deflection. You deflected from him asking you in comparison to how you live in relations to those along the border. That's just the problem here. You think it's perfectly okay for something that doesn't effect you to be okay for millions of other people and quite frankly it's not. He didn't ask you to reflect upon other issues, just upon the basis of the violence and fear some people have to live with. Now if we turned that around and you lived in a situation like that and you couldn't afford a fence you'd be quite happy that the government was going to come put one up for you, wouldn't you? Since you are far removed from any potential harm to come from people crossing across your land it removes you from having any empathy you claim you have. Sure all the other issues are still there but be honest with yourself and admit you'd be tired of waiting for them to solve the other issues and a fence would be a great option to solving your dilemma faster. Yes I could embellish upon those other issues but I am staying on point to what the question was and not deflecting, if I wanted to deflect it probably wouldn't turn in your favor.

He goes on to ask you why you and other progressives feel that advocating for people who struggle the answer from progressives is handouts instead of jobs. What he was trying to get across was wouldn't it be better to be given the same opportunity like your father who came here to have a job to move forward in life. It doesn't matter that he's not going to be a doctor like your father was, what matters is whatever was chose would enable them to move forward in life. How would your father have felt if the answer was you have my empathy, here's a bridge card go get yourself some groceries and we'll put you on a housing list because there's just no need for another doctor because we just imported doctors from India who'll work for less. That's exactly what happened to some Disney workers and some high tech people. Then your dad goes to work doing something else all the while having to find another job every four, five years because his job gets shipped over seas. Do you think that after ten, twelve years of being here your family would have succeeded at achieving their dreams? How do you think you would feel if you were so easily replaceable in the quest for greed?

Yes Trump did raise military pay more than it's been raised in eight years when he got into office. For some military personnel it was the first raise in ten years for those who earn additional pay increases. He also created a spouses program to help spouses gain entry into government jobs, set up a child care benefit package for couples serving and increase mental health awareness programs. Just because the man couldn't word it appropriately doesn't mean he was off track on it.
https://www.militarytimes.com/pay-benefits/2018/02/20/how-do-at-past-military-pay-increases-compare-to-whats-being-proposed-for-2019/