We have acreage that is on a family homestead. Our portion is 10 acres. It's been in the family at least 100-150 years.
Residing on the homestead are the parents, a sister and brother (one owns the home; the other pays rent to them), aunt and uncle, cousins. One cousin lives with the aunt and uncle, as well.
On our portion, we have a 1 bedroom cabin.
Each relative has their own section. Of the siblings, it is divided into 10 acre portions. One of the siblings has opted to not live on her section. She is married, her husband wanted acreage of his own. Understandable.
To answer your question: Yes. I have personally seen how this concept can work and benefit all family members financially. One relative is very smart at coordinating things like planting pines (residual income with annual pine needle baling and cut down every 10? years). Another loves chickens, so she's the resident egg lady. They all also share of their fruit/nut trees. When equipment is needed, they usually chip in on the cost. We'll fall into that fold, when we move out there full time. And when things need repairing, you have one that has strength in electrical work, another more carpentry minded.
The drawback and this is just a huge, huge consideration: Being immersed with these folks on a daily basis, can't get away from it! With that said, keep in mind that these are my in laws not my family or origin! Especially being that we have lived away from ALL family for 20 years, it is incredibly overwhelming. And they can be very pushy with their opinions. Husband and I are accustomed and content with making our own decisions, we do not need other grown adults parenting us. So.. that is a matter of establishing boundaries, which can take time.
We stayed at our cabin a good part of the Summer. Having the cabin now is a huge bonus. There are times when you just can't get away! The minute my husband and I could take a breather to just think or talk, someone else would pop up. If we're in the cabin, they pretty much now leave our family of 4 alone. So, they're so far, so good respecting that boundary. Or the patriach has told them if they want us to come out more and be comfortable, they've got to give us some space.
Once husband has retired from his 1st career, the kids will still have some years in school. We may be going overseas. However, if he finds an aviation job where he just travels back and forth, we will likely go ahead and move out on the land.
We already have the electric and the cabin is a great interim place to stay. while the house is being built.
Being that the land is many generations over paid for..yes. We are far ahead of the game if we live on it. My husband will also have a pension, and we've already estimated that with a very conservative mortgage and the fact that we will already be debt free, we will be able to cover PITI and all basic living expenses on his pension alone. If he stays within the Aviation sector, estimated salaries for his background can range between 65k-100k (depending on what he does), so we pretty much would have the house paid off or close to it at the end of year one. (This is a low COL area so yes, you can build a house for approx 100k.. and we're planning a modest one since the kids will be nearing high school and it will eventually be just the two of us)
Editing to add regarding finances: We would absolutely NEVER pool our finances. They own their land, we own ours. Aside from going in on a side of beef, paying a share on a tractor, we would not be comingling our finances with them. They all have shared minutes on their cell phones and that alone drives husband and I crazy listening about it. There's some things that are worth the expense to not have to worry about Aunt so and so running out all of the minutes for 10 relatives before the month is over... However, we will exercise our option to say, 'No', if offers like that are made.