I am SO curious what you think of specific LMM short stories - namely, The Waking of Helen, The Doctor's Sweetheart, and The Growing Up of Cornelia - but also just all of them bc there is so much going on in literally all of them (not even counting the insanity that is tannis of the flats). apologies if you've talked ab them before but I am intrigued as to if you've read them/have thoughts
Thanks for this ask, I find it really interesting! I also find it very appropriate for this kilmeny shebang, because I think kilmeny provides a very good illustration for this.
I don't think I've read all of LM Montgomery's short stories, although I know I've hit a good chunk of them, so that in and of itself tells you something. There are some I really, really love and that I think are LM Montgomery at her best (The Quarantine at Alexander Abraham's), but I find a lot of them to be LM Montgomery at her worst. Some of them encapsulate LM Montgomery's strengths in a really potent, concise way; a lot of them emphasize her weaknesses in parallel.
Because I haven't read a lot of them since I was a teen, I mostly have dim memories of the ones I liked, or of ones where I was like hmmm...that's funny, or the ones that I liked but now looking back am like hmm...that's funny. I used to love the Growing up of Cornelia quite a bit, but now I squint at it for obvious reasons. I LOOOOOOOOOOOOVED the fake dating one because I thought it was hilarious (this spinster lies to the town about having someone courting her, someone she completely fabricates - only for a man who happens to fit the description to a tee show up in a sheer shenanigan of fate). The Strike at Putney is my sister's favorite (the women of a church go on strike to combat sexism).
So overall, there are some jewels in in the mix. The form of a short story is such that in some ways, you have to strip writing and storytelling down to its bare elements. As such, I think the form of a short story is particularly well-suited to demonstrating Maud's strength of humor. When they're good, they're good.
However, as referenced, that often means when they're bad, they're bad. Some are technically well-written but gross in plotline (these are the ones that tend to be the ones I liked as a child, but as an adult..); a lot are both disturbing and imo pretty poorly written, much like a certain novel we've been discussing lately. We have Tannis (YIKES), the Education of Betty (YIKES), and others which kind of pull back the curtain on Maud.
LM Montgomery was no angel, and even beyond aspects of her you'd expect historically, she was just...kind of mean. I remember reading a letter of hers where she visited some equivalent of a girl scout troop and frankly talked about how she couldn't imagine any of the girls finding husbands because they were so plain and ugly. You see it pop up in her books, but it pops up a lot in her short stories as well. In the end, to answer your question in a general sense, I feel like overall the short stories have more kilmeny's than anne's.
Regarding the specific stories, I'd have to reread them. We did discuss the Growing Up of Cornelia on here a while back - I used to LOVE that one, but now as an adult I'm like more errrr. It is interesting to me because Sidney is the Dean Priest figure that ever haunts LMM's work. As for The Waking of Helen, iirc this is @mzannthropy's favorite! Unlike Kilmeny, it actually commits to its premise and so I think it works. I'm not really familiar with the Doctor's Sweetheart - I looked it up and nothing rang a bell.
For my favorite short stories (You didn't ask, but I shall answer anyway) - here are the ones that I remember even years later:
The Quarantine at Alexander Abraham's: iconic, in a word. endlessly quotable. A spinster woman who hates men quarantined with a confirmed bachelor who hates women? Much like the blue castle, this takes a basic fanfic trope (for tbc, 'where is my wife;' for this, quarantined together) and so successfully executes it you're left with your jaw on the floor.
The Strike at Putney: this is a sister's favorite, and I can see why. Women of the church learn that a missionary will not be allowed to occupy the pulpit to speak because she's a woman, and so they go on strike. It's also a emphasized critique of the undervaluing of women's work.
The Materializing of Cecil: GOD I REMEMBER LOVING THIS ONE. This unmarried woman is embarrassed to be unmarried at forty and so flagrantly invents a lover to her sewing circle - only for a man who fits the description to SHOW UP. It's hilarious. However, as a content warning, I reread it to find there is less than fantastic description of a Chinese man near the end.
The Little Brown Book of Miss Emily: guess what? this one is in first person, and that person is ANNE. 😱 this one...it's sad, but it always stayed with me. I have read quite a few lmm stories and forgotten most, but not this one. Also, its final line is beautiful to me.