The biggest problem I have with him is that he's not good at making a case for his positions to those who don't already agree with him. I watched the debate with PaulsEgo on gun control, and even though I align much more with Razor on that particular issue, there were so many instances where I was smacking my head because he should have stuck to presenting actual figures which state that the correlation between gun ownership and crime rates are tenuous at best. Instead he spewed a bunch of cliche pro-gun lines that aren't going to convince anyone who's anti-gun, and allowed himself to be sidetracked by minor shit like debating whether or not Phoenix is a big city compared to L.A. I haven't watched the Kyle debate, but from what I've been told its basically the same shit.
He's obviously biased by nostalgia to a large degree. Also love how he pretends as though the 80s were somehow less censorious than the 90s considering that was the height of the christian theocrats power in America. Also the self-esteem movement, which in many ways was the precursor to the type of political correctness we see nowadays, was also at its strongest in the 80s and only started to be heavily criticized and satirized in the 90s, which he claims was the "dawn of political correctness" probably due to Bill Clinton or some shit.