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Why don't they sell the horse? I know Caroline loves Chestnut, but keeping a horse under those conditions is just cruel to the animal. Not sure how old Chestnut is, but he seems healthy and has a very gentle disposition, halter broke and even comes with his own tack. That could fetch a good price and they could insist that Chestnut only be bought by someone who will and can take good care of him.
Out-of-universe, because then they would have one less hook to make their show different and, so the writers hope, more popular. In-universe, probably because Max and Caroline each have a soft spot for animals, Caroline's a spoiled former rich, naive idiot and has bonded with Chestnut over a period of several affection-starved years, and Max has no proper equestrian training (she treats the horse like a giant dog).
Also, even though the horse belongs to Caroline, it could technically be considered stolen property. (Remember, the Channing family's assets had been siezed, meaning the horse and everything else they owned were property of the federal government, so taking it was a criminal offense.) It's not exactly common for people in their neighborhood to own horses. If they sell it, they might raise questions about where it came from.
This question borders on Fan Wank. Why don't they sell a beloved pet for the money? Really?
The issue gets addressed in "and Reality Check". When winter arrives the horse can no longer live in the city and they need to find someone who is willing to house and feed it over the winter for free. One stable owner even points out that the horse is not in great condition due to the lack of exercise. Caroline is in denial but Max gets her to see reality even if it hurts.
Why don't they invest the cupcake fund? At the end of each episode, we see the value of the cupcake fund fluctuate depending on how much they earned or spent during the episode, but it never seems to accrue any interest or dividends, or undergo capital gain or loss. They use the money from selling Caroline's rings to buy the Bluestar oven in purple in "And the Pop-Up Sale," which would count as a capital investment in their own business, but that's about it. Why wouldn't someone of Caroline's financial savvy invest their savings?
She's never had to live day to day and it's obvious that she's quickly learning that just getting to tomorrow has a value in and of itself. The better question is how the number remains so static. Even when they buy things that are in the hundreds of dollars somehow their income is almost always exactly the same as their expenses. It's like asking why they apparently don't advertise at all. As a small business owner I can tell you that 250 copies at kinkos is only 50 bucks when you realize you can cut an normal peice of paper into 4 (or more) peices they simply aren't maximizing their business but that's fine since Max has no experience and Caroline isn't use to being ground level she's used to observing top tier stuff.
How does that answer the question? What does the fact that she's never had to live day-to-day before have to do with her apparent decision not to invest their (admittedly meager) capital? Wouldn't her natural reflex be to invest it? Even in a simple savings account it would generate at least a little income, though someone as financially sophisticated as Caroline would know better than to put her money in a savings account.
For that matter, why doesn't Caroline try to get a better job, say at a bank or even one of those Payday Loans places? Someone with her education (not to mention connections) surely has better job options.
Probably has something to do with the current state of the Channing name. It's come up a couple of times before that people are hesitant to associate themselves with Caroline simply because of who her father is.