I think that he can be unnecessarily insensitive, and his arguments tend to fall apart when it comes to religious issues on account of his devout religious status.
Like, okay, on transgenderism. He says that it's a mental illness and refuses to refer to people by their preferred pronouns, saying that "they can't force me to lie." Transgenderism is not a mental illness anymore than heterosexuality is. It's just how some peoples' brains work. Shapiro says that it's an illness because it contributes to a high suicide rate, but that's likely more because of how society views transgender people and refuses to accept them than anything. I don't think that biological men can ever be literally be biological women (that part is scientifically untrue), but like...what the fuck does it matter? If someone wants me to call them something or treat them a certain way and it literally does nothing to hurt me, then why shouldn't I? With Shapiro, it comes down to the fact that referring to a "he as a she" (as he puts it) goes against his religion. And while I do agree with him that forcing anyone to abide by a practice that goes against their religion is bad and shouldn't be a thing, he could just chill and be less of a dick to people who already have a rotten deal in life.
His religious bias influences his opinions on issues like abortion, too. He considers abortion to be murder, when it really isn't. By his standard, "potential life" is the same thing as life. And it's not. If you held a petri dish with a first trimester fetus over a cliff along with a baby and were given the option to save one, you would save the baby 100 times out of 100 because it's a baby. It is different. But according to Shapiro's religious beliefs, it's not, and so he's biased about the issue.
All of that said, he generally advocates for "hands-off" politics. Religious bakeries shouldn't be forced to cater same-sex weddings, and in return, same-sex weddings can take their business elsewhere. I fundamentally think that this is what America is founded on, and it's important. But yeah, Ben is kind of a dick in the way he says it.