Ooooh, I wanted to love

this but the best I could end up giving you was a like

. Points were lost when Regina, the capital city of Saskatchewan, was pronounced Ree-Geena instead of Ree-G-eye-na (hard I sound; yes, it does rhyme with a ladypart).
If they were rural, or lived in a very small town, the mailman was probably a friend who maybe did things on his own schedule, which might have been common back in the day. Not widespread by any means and as has been discussed over and over here on the CB, many of the anecdotes you remember or were told by your Saskatchewan cousins were unique to them and NOT representative in any way of being generally Canadian.
Yes, absolutely. Major medical (doctor's visits, hospital care, care for chronic diseases and cancer care, among many other things) is covered by health care and since it is a provincial jurisdiction, what is covered may vary somewhat from province to province. Things like dentistry, vision care, some mental health services, chiropractic, physio and rehabilitation, naturopathic and homeopathic medicine and most prescription medication is NOT covered. Those things are either OOP or covered by supplemental insurance which many of us have as part of our employment benefits. Most provinces have some sort of supplement for low-income people that will pay for all these extras. For the vast majority in the middle-class, it's kind of like in the States - have insurance, pay for it yourself or do without.
Yes.
Fair enough. Most Canadians don't care much about Spain, or Norway or Singapore - I see it as the same thing. And we shouldn't take it personally either. I doubt most Americans know (or care) any more about Mexico than they do about Canada.