I can't stand him to be honest, and I'm surprised that anyone would find that article the best thing they'd read on the topic because it seemed to me all it revealed was his bitterness about his past and his desire to distance himself from his background and family. He's the same age as me so lived in Tory-ruled Britain until he was 21, so if there was a problem with the benefit system stopping his mum from working then it happened under a Tory government, not Labour, though his comments about his mum are pretty horrible and I agree with the pp who said she may have had a mental health issue if it was all as he described.
I don't know if he was trying to blame Labour for the oh-so ridiculous shenanigans his 'lefty' teachers inflicted on him, but I was at school when he was under the Tories and remember temporary classrooms and a shortage of books. As a teacher under Labour, everything wasn't perfect, but there was an influx of funding and PPA was introduced, which made a big difference to my working life. Then the Tories came back and we got Gove...
Also, all that shit about his dad and the union. Typical right-wing bullshit trying to discredit the trade union movement which has given us many of the rights we all, not just Labour voters, take for granted and benefit from. And I notice he has no actual details about how his dad was 'bombed' from his job but just seems to be vaguely trying to pin it on some kind of betrayal from the union.
And 'small-c conservatism' doesn't mean what he seems to think it does. The expression he was looking for when describing his attitude to his mum was petty, small-minded snobbery, I'd say.
Despite what he seems to think. he is far from being the first working-class person to vote Tory. He's obviously got some issues about it as it's all he ever bangs on about but he's probably better off accepting that he's got some hang-ups about the area he grew up in nd the way his family was and voting Tory is probably partly a way of distancing himself from that. Maybe he'd benefit from some talking therapy to come to terms with things? Don't get me wrong, there are lots of problems with Labour now, but this is just self-serving twaddle from someone who who protests too much about why it's all Labour's fault he's chosen to do something that goes against morality in many ways.