Modern Commentary
Kimberly admitting that she needs help? Yes. I mean, she's come this far. She's talking to her mom and everything. No point beating around the bush here.
End-of-You-Say-it-First Kimberly would have gone in there with a plan, including reasons why it's in Ms. Taylor's interest to give her the money. That's part of how Kimberly grows throughout the series.
I'm not sure what Ms Taylor thinks will happen if Kimberly gets almost-but-not-quite-enough money. But Kimberly has always been good about finding a little money when she needs it. She's resourceful that way.
Traditionally, Kimberly's emergency plan involves overcharging Brisbane, which isn't going to be a great idea here.- Terrence

Modern Commentary
This story - the rise and fall of Mr. Taylor - got built as things went on. A fuller version got told in The New Guy, three years later. And, to a lesser extent, throughout the entire comic.
Bud the pool boy isn't mentioned there, but there was a lot going on between Kimberly's parents. Kimberly's version of this is probably also true.
I'm pretty sure we had the basics of Kimberly's parents' backstory developed at this point, and part of it was finding a place to explain it and part of it was just deepening our understanding of it before we did. - Terrence