I recently read this and I thought it was a great examination of what you should expect at each price point of wine: How to find the sweet spot in the cost of a bottle of wine | The Hub. It’s really aimed at Canadians, but it can apply elsewhere.
I am still a fan of cheap wine, but I find myself drinking closer to the $20 price point now. In Ontario at least, that seems to be the price at which wines are consistently good. There’s nothing wrong with buying wine at all sorts of price points. You should just know what to expect.
Speaking of cheaper wine, this is worth a read: The Science Behind Your Cheap Wine