He's done some nice videos but I must admit, having lived 20 years in Canada, that I am betting he's collecting UI in the winter months which I'm not a fan of. In Canada it used to be that you had to work 20 weeks before collecting a years worth of UI, then 10 weeks after the first year. Too many took advantage of that so they changed it to 20 weeks and 20 weeks. I last left in 1995 so maybe things have changed but at least back then it wasn't uncommon for someone to work 5 months and take 7 months off doing basically what he's doing (or variations on the theme).
Not meaning to rain on his parade, and the Canadian government didn't seem to discourage this back then but it isn't as if people could do this without either A: lots of money saved up from working months B: the dole paying the bills during non-working months or C: some combination of the two.