Exactly! It is actually hard to estimate the quality of a product. And when you can't, most of the time you go for the cheaper one (unless money doesn't matter much for you).
Not true. New entrants to markets often will price to undercut markets (see Uber and Airbnb in their early days). Also loss leaders are a very much a thing.
Over time markets do typically stabilize and this could be true.
As for Uber, I guess you're right in many regions. But there's a plethora of Uber competitors around the world, offering a worse experience for a cheaper price.
In 100% of cases, the cheapest product you can find will be of significantly worse quality than the second cheapest product, without bringing much savings. The rest is edge cases.
As you pointed out, I'm talking about reasonably mature markets.
I think it's an interesting heuristic, though.