Not that this is a guarantee or anything, but I have found that by going over your bike carefully once a week on a trip, to clean, check bolt tightness, and yes to check tires, is just a good idea to help spot weird stuff going on or at least be aware of things like a little sidewall damage....To him this "just happened" or was "bad luck" but it happened because his tire was worn and he had no idea.
Ditto this. One of my favorite quotes from my days as a first responder is "You make your own luck." We often downplayed some successes, saying how lucky we were that something didn't bite us. But in fact it was training, preparation, and good experienced leadership that kept us out of trouble.
Every time I put air in my tires (and now I need reading glasses just to read the darn gauge), I check the wheels for tire wear and bearing play.