One thing I often see permies mistake is not putting a dollar value on their time. I pay a lot of people to do things I can definitely do — I have contractors remodeling the garage right now, I pay a full-time caregiver to help my parents, I pay an accountant to do my taxes, etc, etc. These are all tasks I'm totally capable of doing, but when I factor in the value of my time, I lose money to do them.
As an example, if you earn $50/hr at your freelance job and a housekeeper costs $15/hr, that means you earn $35/hr for every hour you hire them to do work since you can earn $50 in that same hour. But even then, that math is off because they are probably much better at housekeeping than you are, do a better job, and do it in less time.
It's not always clear what your hourly rate is, especially if you work for yourself. But I assure you, with enough calculations you can find a number. Even if you're not making money. Let's say you're willing to go into $10k of debt to build out a pasture that will require an extra 5hrs/week of your time for a year. You have decided that your time is worth $38/hr ($10k/(5x52)). If a housekeeper costs $15/hr and housekeeping time directly conflicts with building this investment, it's an easy choice to spend the money on a housekeeper.
But of course, you're going to have to mesh this money-centric view with your values. Maybe you enjoy cleaning your kitchen. Maybe you value self-reliance more than your hours. Focusing on rates of return is a great way to manage your finances, but not always a great way to manage your happiness.