Hey Nathan, as another user mentioned before, you should definitely look into Dave Ramsey's books if you're looking for great financial advise. I also recommend a book by Gary Keesee called "Fixing the Money Thing." These authors get into great detail about the benefits of living debt free and paying cash for things. Some of the advise may be common sense, but these books are very motivational and have greatly influenced my interpretation of living frugally, avoiding loans, and any other type of debt.
My wife and I are also in our late 20's and have 2 kids (3 and 6); we are also homeowners who are looking to make the transition from urban living to sustainable farm living and a debt free life. Like everything else in life, there are some risks to this transition. Since we have little to no savings to fund this long sought dream, we will be using the proceeds of the sale of our home. Thankfully, the market here is good enough that the sale should yield a significant profit.
Now the next step: Since we do want a buffer in order to afford some losses and other unexpected costs, we have decided not to purchase land. Instead, we searched for opportunities where farmers or retired farmers are seeking to have someone farm their land, exchanging rent for farm labor, land maintenance, food, etc…,while still allowing us to have our own enterprise. This cost effective approach, will also provide us with invaluable advise and training, that will minimize our learning curve. We also feel like it is a low-risk approach.
In our case, we were fortunate enough to find a nice couple who own 100+ acres of land who wish to see someone work the land and establish their own enterprise there. The farm is already equipped with a large greenhouse and infrastructure needed to operate a small to medium sized poultry operation, as well as hogs, and other small/medium sized livestock. This opportunity came about after months of online searching, and while visiting family in North Carolina, we drove out to meet the couple and discuss the opportunity. While the couple still have city jobs, they still live on the land and grow their own food there.
Living arrangements: The farm has a small studio-like guest cabin, but it would not be big enough for a family of 4. Therefore, we have studied our options and found that the best living arrangement would be to purchase a 2 bedroom prefab cabin (15x40) and have it dropped off next to the small cabin already in place. Again, another low-risk approach, if we decide to purchase our own land someday, the cabin can easy be picked up and moved (it is a portable asset!) Another big plus is that the lot already has water, electricity, and swage hook-up on site.
Hopefully, this gives you an idea of what other crazy folks are doing out there and encourages you to find the best path for your family (I will also be blogging about my journey, for those who are interested). Lastly, I will add that anyone taking a similar approach of farming on someone's land, to establish a contract outlining all the terms and conditions. This way you can avoid any future conflicts or misenterpeted expectations that may hinder your relationship with the land owner.