Yep... I'm too nice.
Don't get me wrong. I am a very friendly person and help out my closer neighbors all the time. They borrow all sorts of things, and in return, I borrow their things, services, etc. It's give and take. This guy seems to only take. He is a rookie, and I knew that when I saw him hooking up his tiny tractor to my large tiller. But I couldn't morally stop him after saying yes. I shouldn't have said yes. When (not if) I get my tiller back, it will be the last time he borrows it.
I am afraid that he will damage it. And if he does, I will pester him about repairs, which will likely fall on deaf ears.
I have spread the word about him to my neighbors. Some of which have no idea who he is.