I love linked stories, my own novel, The Gilda Stories, is just such a confection. There is something about the 'random' way a reader can touch down in the lives of characters when they are in stories rather than a direct narrative. Back in the day when hypertext was all the rage it seemed like it was supposed to give you a new amplified/random/deeper perspective on the story. All it did was send me through distracting mazes, but that's just me. Short story collections that surround a character, theme or place take me on that journey---give me many different views of something that take me deeper in through a circuitous route.
And Olive Kittredge needs a circuitous route because she's tough. She's the kind of woman I used to fall in love with: upright, definitive, laconic, demanding, opinionated. On the outside she seems relentless and judgemental...and she is...but not just that. I grew up in New England and this is the kind of character of legend back there. So it felt like I was meeting some one I may have known in the past. These are women who see everything but don't talk about it much unless something needs doing. Still they sometimes don't see their own flaws which are big Burma Shave signs to eveyrone around them.
What feels like witholding sometimes is. But sometimes it's simply not talking when it doesn't seem like it'll do much good. Olive is too obsessive about some things (like her son) but unyielding in her commitment to folks if they need help.
Some folks thought the book was too depressing to win the Pulitzer. Fortunately the Pulitzer jury didn't think so.
You will want a stiff drink when you're done. Maybe a supersize margarita.