So, why would the farmer use it then?
He will now pay e.g. $1000. Tillable will offer $1100 upfront to the land owner and then "offer" it to the farmer for the low price of $1200. Since he can't just farm on some piece of land 500 miles away, he can either pay the new price, or stop farming.
Tillable offers no significant service here. It's not that there's a lot of land sitting idle because farmers and land owners have no way to come in contact, they are not solving a problem, they are just injecting themselves to extract rent with VC money.
The scenario you describe is possible only if there is a lot of land that's severely mispriced / underpriced - in which case the price should and would get corrected, and after that the arbitrage opportunity disappears because, as you say, the land owner can come in contact directly with the farmer and make arrangements.
Basic human decency? These are often long-term relationships between neighbours, whose families lived next to each other for decades or hundreds of years.
EDIT: for the same reason, I don't think Tillable has a chance of working, and to the extent it does, it's actively destructive.
1. Want to extract as much money as possible will turn directly to the farmers willing to pay top dollar to maximize the take.
2. Want to build solid relationships with farmers will turn directly to farmers to find a suitable fit.
The question presented before your original reply was in trying to understand where Tillable fits. Your answer did not provide that information, and your follow up still does not attempt to answer the question.
Your edit seems to suggest that they don't fit, as was already established, which leaves us wondering what your original response was for?
Land owners are not in the business of maximizing profits at any cost, but if you approach them with a much better offer for their land, they don't see the ways how you're able to afford that offer, much like the smart phone buyer does not know why it doesn't cost $100 more. When people profit from something, they are usually not too concerned with the details and accept that things happen that they wouldn't allow if they knew about it, by turning a blind eye (blinded by the profit, you might say).
(Worth remembering that disrupting evokes, particualrly in this context, the picture of a disruptor - a weapon used by evil Klingons and sneaky Romulans.)
Your explanation makes me think of a paraphrase I like to post: the only thing necessary for the triumph of evil is to separate good men from it with enoungh layers of indirection.
Farmers approach landowners with better offers all the time with no qualms about paying top dollar to get it. Being a farmer myself, I can tell you first hand that competition for land if fierce. Sometimes the approaching farmer is taken up on the offer, sometimes not. But I see no real indication of pent up demand that isn't being satisfied because people cannot figure out who the landowners are. There is literally a land registry, if all else fails. But rural communities are small. You already know who owns what, and conversely who farms what.
It remains: Where does Tillable fit?
As TeMPOral mentioned in a sibling comment, mostly their long-standing relationship, and his non-predatory business model. Right now, he's a land owner. If he uses Tillable, he's a property investor.
In essence, tillable becomes the only landowner
The same reasons that have kept my landlord from raising the rent me and my partner pay in over 14 years now. When we asked him if he didn't want a raise (we were concerned he was not making enough and would have to sell the house) he said that no, he prefers to know that the house is rented long-term and he doesn't have to find a new tennant every few months.
So, basically: stability. Some people tend to value that very highly. I know I (and my partner) do, which is btw the reason why we've stayed in the same place for over 14 years. That and all the scare stories of asshole landlords we've heard from friends who moved frequently (we're in the UK btw).
The vertical integration Uber envisions is self driving cars. Any company which has a foot in the hauling market will have an advantage over a purely self driving research company. The vertical integration of Tillable would involve things like buying the land, renting out machines, completely automating the work, etc. Something like that.