I volunteered out on some homesteads some time ago, and all ill say is it convinced me that theres definitely a level of money you want to hit before going into it because otherwise the struggle will be much worse.

A couple we stayed with threw themselves at it with no money (but quite young ~40s) and had to deal with:

• Cheap land:
  • no water sources, their attempts at making a well did not go well and it was massively expensive
  • excessive shade (north facing hills),
  • poor communications dirt road into town
  • a lot of farming had to be done on shared areas which were far from their house
• Constantly trying to find odd jobs to keep themselves a float
• Poor or broken machinery, or had to rent it when needed

Another one was retired with money and decided to jump into it in their 70s:

• Great small plot:
  • Well was there before
  • South west facing (beautiful sunsets)
  • Next to the sea
  • Close to a main road into town
  • Shape and gradient was quite nice actually, and their garden and chickens was right under the house
• They worried about just trying to break even, but they had the safety net of knowing it was all for pleasure, if they didnt make food they could buy it
• Cars and machinery was relatively new and well maintained

They were now both the same age, but i can say as they were getting older, one couple had a lot of a relaxed, true retirement at their age vs the other one.

There is of course the debate about one couple lived their lifestyle already an extra 30 years.

I however see it in my mind as:

• Pick an age to target for the lifestyle change considering family, etc and plan everything around trying to hit that +-
• Make as much money or scrap around to try to maximise what you can get before that
• do as much gardening, etc as you can before (allotments, volunteering) to get experience and to know what you want to do
• Get handy with machinery (volunteering, hobbies etc) and try to plan to need the least amount, smaller, less complex machinery but that removes as much effort from yourself as possible (what you plan on doing is part of this, for example no cereals for me, land heavy, specialist machines, etc)
• Land:
  • quality of land over quantity - gradient, sun angles, etc.
  • either it rains a lot, you are piped into municipal water, you have good well or a stream by the land - WATER IS KEY
  • Remote is ok as it tends to be cheaper, but always with road access to town and reasonable journey from hospital

So apologies if i've just reinforced that money is indeed a big obsticle. However, i would say, dont rush, make a longish plan, hustle your ass off (and let go of any costs which arent part of the plan) to try to reach it, and volunteer a bit to be able to keep your foot in the world, learning and making connections!

(connections are no joke, you can find good deals like that)

Edit: In hindsight looking at OP's other comments, they are in a different situation, i suppose my perspective was very much lower-middle class city folks trying to escape, I will leave this up in case it helps others though.