In 10 years of living in NYC (Manhattan and Queens) I never bought a container of milk that lasted until the expiration date. None of the markets (then, anyway) had enough refrigerator space and new deliveries frequently sat on the sidewalk for extended periods before being shuffled indoors to a cooler corner. As a big milk drinker it took me some time to get used to the flavor of fresh milk once I moved back to America with modern stores.
I still find that older markets, even in the ‘burbs, frequently have one old chiller case, usually at the end of an aisle, which isn’t functioning. In my area that’s where they usually keep the horseradish and creamed herring, or the yogurt. I don’t buy from that case.
As for the Boston Coffee Cake (a delightful product), could be an example of a store trying to avoid having to rotate merchandise. (And I’d be disappointed if Big Y did that – it’s more what I expect of the current management of Star/Shaw’s/Albertson’s where they re-date the meat.)
As for personal practice, we look at expiration dates when we buy, except when something happens to be out of date in which case we forget to check and it starts crawling on the kitchen counter. If it’s not perishable, once it’s in our possession it’s fair game.