I have had these Top Siders for about 18 years.
They have been re-heeled about ten times. Re-soled just once. Then, finally, last month, I had to re-stitch them.
Why don't just I throw them away and start over? Well, a big part of it is that I'm not willing to spend the money for a new pair. (About $72 now.) Another reason is that they are broken in perfectly. They slip on so easily that they live by our front door - so I can slip them on to go out for a minute.
So yes, this cheapness can be a bad thing - when it gets to be some sort of bad pride, like when we had an ancient Volvo. I was always saying how old it was - but it turned out to be the worst use of money we ever did, when it died in the desert. But that's another story.