I thought most people I've spoken to over the years have seen the Spanky's mother/Daisey Dimpeles connection.
Daisey wants to win , it's her idea to go on stage, her mother can't afford to back her daughter in stage career hoping to win the prize to buy the dress.
Spanky want's nothing to do with this it's all his mother's idea. Spanky's mother tells him she want the prize money he can do with it as he pleases.
Other's say Daisey wants to win to get her dress and it takes Spanky's mother's dress to win it. But Spanky had already won the prize before she was stripped.
When Spank asks permission to give Daisey the prize money his mother smiles nad says she only wants him to be a big hit as Spanky says to Daisy " Girlie ,The dress is in the bag". Of course the viewer would know it will be his mother whose the girlie whose dress is in the bag later on.
I think it was intended that Spanky's mother and Daisy shared so much in common . If you watch when Daisey is running off the stage they play a laugh track that is the same as when Spanky pulls the stage prop in front of his mother and we see what she looks like.
It's funny that when they are laughing at her she can run off the stage but Spanky's mother is trapped and frozen in place to be howled at at the audience's will.
I think that Daisy is wearing a hat very similar to the ones the girls are wearing from the Flora Dora Dollies. This was a time where everyone wore a hat. If you look at the friends of Spanky's mother all women are wearing hats except the ones who live there. All the mothers backstage are wearing hats. I really don't see a connection with the hats or Daisy's dress looking like a slip. You might have something with the poles both wind up on stage with though.
The title "Beginner's Luck" I think is huge for this short. Daisy flops due to stage fright. Clearly she was the worst act as she was incapable of anything. But she wound up with the prize money. If it wasn't for Spanky's speaking with Daisy before he would have just walked off stage when his mother becons him . Spanky's act isn't that good either. His real act would have fallen far short of the Cabin Kids act. The way he trys to fight and get through the barrage of his friends make people think he is doing a spoof act of a Shakespearian play. It's all LUCK either good or bad that make things happen.
The similarities between Daisy and Spanky's mother are there for sure. When Daisy runs off that laff track is added in , also Spanky's mother can be seen saying something to the grandmother like I feel sorry for that child or something like that. She is of course unaware that she will get it much worse when Spanky's act is ending.
The ironic ending the child gets her prize money for her dress and Spanky's mother looses her dress and is made a fool of in the process.