It would be very difficult, because you're playing by the wrong rules.
Let's start with this big one: Most European medieval societies lacked enough disposable income to purchase your food.
Then let's move to the next big hurdle: There was no large scale food preservation or transport infrastructure. Most of your crop would simply rot (or feed rodents).
But let's look past those: If you did manage to sell the crop for a large sum, there wasn't much banking infrastructure in most places to handle money safely, so all that coinage is where? At home with you in a strong room? Uh-oh, you just became a target for bandits and corrupt local leaders.
And that's before we get to not-very-effective rule of law (by today's standards), encouraging those leaders to trump up charges and confiscate your super-farm for their own enrichment.
You're playing by the rules of an industrialized society: Disposable income, easy and cheap transport, a whole industry of varied food preservation and value-added products, easy/cheap/safe money movement, and laws that are applied reasonably fairly.
Folks in the Medieval weren't stupid. But they had different rules for success. To be successful, you need to be a bigshot: Rich and Tough. You need an ostentatious mansion and your own company of goons to guard your money, guard your robots, and to keep the other upwardly-mobile nobles from swindling or intriguing or otherwise stealing the source of your wealth right out from under you. Be prepared to pay monumental bribes, er I mean 'taxes', to the local feudal lords to leave you alone (and prevail in disputes), smaller bribes to fund your own private intelligence network, and to fight the occasional duel or resist assassination when a forged will is about to turn up.
Oh, and it would help if your farm turned a profit to pay for all this protection. Make sure to pop in occasionally and see to the actual business. Likely multiple businesses, as you will become a pioneering mass waggoneer, too. And a huge value-added food processor (milling, drying, smoking, pickling, etc.) And, by necessity, a banker. You're going to need a lot of goons to protect all that infrastructure and industry.
Because of heavy use by all your industries and all those wagons and all those workers, your roads are likely to be awful...especially during the muddy seasons. You might consider inventing steam engines and railways a few centuries early.