Well, he would likely be a telephone line repairman.
In Ottawa Bell has a company that works for them, but isn't a part of their company if I remember correctly called Bell Technical Solutions.
You start off just above minimum wage. However, you get a dollar raise basically every 6 months, so 2 dollar raise a year.
Assuming he goes into that profession shortly after getting out of high school, but the time he's 29, assuming he started there at 18 and had Wayne at 25, he would be averaging over 30 dollars an hour working your 7 - 4 type job as he would have seniority to get that by thar point and likely able to get some ot. Even though Ottawa is fairly expensive (housing prices have raised over 100,000 dollars in the past year if I'm not mistaken) he would likely be able to still afford a place and put Wayne in hockey. His wife would also be working. Not sure if she did in the real timeline.
In short, he would likely just be able to.