A discussion about the money.
Economically Speaking, Homesteading for profit makes very little sense. Let's discuss our homesteads in terms of small farms. 7 percent of U.S. farms command roughly 70 percent of total farm sales. Those large farms are profitable, but “the other 93 percent of farm households have negative farm operating profits, on average, and draw most of their income from off-farm sources". Fruits, vegetables, meat and dairy are all commodity items. They are produced at scale and in volume in order to be profitable. So if you imagined supporting your family selling tomatoes by the side of the road, think again.
Waking up early to feed the animals, tend the garden, till a field, sow seeds, reap hay. By the time these daily activities are over it is probably supper time. So if the output of this labor, which is unpaid, is commodity items with very low profit margin, why would anyone do this?
What viewing farming in purely economic terms doesn't take in to account is shocks to the system. While certainly not predictable, every complex system that effects us, and is therefore studied, has published statistics on the frequency of negative events. Whether this is how flood plains are measured in terms of how frequently you can expect it to flood, to how recessions on average happen every 10 years or so. It has been a while, but we can now add pandemic disease to the picture. Certainly there are other concerns in life; wars, economic collapses, large scale natural disasters. But it doesn't make much sense to spend your time or resources planning for something that only happens once every hundred generations or so. However it can be quite useful to plan for the ones we will almost certainly see repeatedly in our lifetimes.
How can a homestead can insulate us from shocks in the system? From food prices to power outages, the more self sufficient we are, the less we are impacted by the outside world. It is unreasonable to expect to be fully self reliant. While it can be done with a dramatically lower standard of living and expectations, even the Amish have realized the need to form communities. Some division of labor is still practical. So the question becomes one of degree. What things must we be able to produce on a daily basis, vs what things must we be able to produce in an emergency? How long should we be able to go without outside help in each area; food, water, electricity, gasoline, etc.. A reasonable answer to this question provides stability.
Before rebar was added to concrete, masonry homes tended to collapse in earthquakes. This is what you can achieve with a homestead that will not be possible in a quarter acre suburban lot or downtown condo. Can you grow or preserve enough food to last a month? How about six? Can you generate your own electricity with solar to meet some of your needs (such as refrigeration and lights). And unlike the prepper notion of a basement full of food, can you continue to replenish your resources without access to outside inputs? Because ultimately this is what makes a system resiliant.
People often ask questions looking for a simple answer. But the answer to almost any question about how things should be done is 'it depends'. How can you afford to homestead, and gain the benefits of anti-fragility, but also more control of your own life, more time in nature, etc.? That completely depends on your circumstances. My wife and I put 20+ years each in to the corporate grind living in a city while saving enough money and building equity in a home so that one day we could retire early and build a homestead. That doesn't solve our problems long term, if we only draw down our money we will be on a fixed income and have no ability to deal with shocks. It will be very fragile. So whether you can buy a piece of land outright, or you need to work for decades in something unrelated, or you go inbetween and work on someone elses farm, lease land and eventually buy your own. Your answer will be unique. But remember the principles of anti-fragility and sustainability. Be in a situation where you can ride out shocks. A good counter example of this is taking out loans. If you have a large payment that you barely make each month, it will only take one to two months of loss of income to lose everything you have built. This is the most fragile situation you can find yourself in.
Some families will have one member full time on the homestead while their partner holds down a corporate job (which can be a good way to get healthcare as well, speaking of a fragile point in your system). Some people will try to do things that augment or supplement what they were doing. Here are a list of ideas, but it is in no way comprehensive, simply to get the creative juices flowing.
Don't give up on the homestead itself as a source of income. It can be beneficial to diversify, but the more you can generate revenue from activities you would be doing anyway, the more you are leveraging your time and energy.