But I bet he checked whether he could afford the roller before he agreed to do the work. Either that or put it on a credit card with the intention of paying the bill after you paid him, much like taking a loan in game and paying it back after fulfilling the contract.
Much like me knowing I'd have enough to afford the header after selling my crop.
Why would I take out a loan instead of selling my own crop?
One of the main activities in the game is collecting crop to sell, to buy new stuff.
Sell your crop. The contract is not going anywhere in the few minutes it will take you to sell a few loads
Yes, I know how to work around it. New players might encounter the bug like I did.