I think you have analyzed it fairly well. At the end of the day, you generally get what you pay for and a known brand name with a good reputation is likely to work MOST of the time better than a lesser brand. No different than buying a no name brand TV vs. a known brand like Sony etc.Spent some time on net searching for others who have experience with HT Roadside. It doesn't sound good. None of them seemed to have my problem with their communication. But what I gleaned, was that they use small contractors to provide service. Some not too competent, it seemed. Probably best to be avoided!
So getting back to decision making. I have concluded that HT Roadside is next to useless. Other "free" services don't seem better. Other paid services like CanTire's have limitations - I don't want to be towed to a crappy tire
There is one other I could consider. I have my classic cars insured through Hagerty who have their own plan. It does seem very good and costs just $55/yr. But how well it works in Canada is another unknown and I would not be covered if driving my wife's car. (But OK in Subaru while still under warranty)
CAA is a known entity that we have had good experience with and works regardless of what car we are driving or even a passenger in. Cost just one users smart-phone monthly fee or one Starbucks a month (Neither of which I use)
So that will be it - Thanks for helping me decide!
I would say though that if someone's EXPECTATIONS are in line with what they should expect from a free service, that may be enough to suit them. It's usually the difference between someone's expectations and what they actually get that are out of line. Like paying for an economy seat on a plane and expecting a comfortable flight in terms of space. Then they complain about it when that doesn't happen.