I adopted a policy several years back, if I like you and if you need help, then you really need my personal help and the tractor is just a tool to get a job done and may or may not be used. I once loaned a friend tractor with a 15' brush-hog to clear a overgrown pasture, I warned him is was designed as stalk cutter and would throw stuff out the back a long way, so make sure the field as clear. Well, he parked his truck in the field, hit a piece of metal and broke a door window out of his truck, had the basketballs to ask if I would pay or claim it on my insurance.
My wife does get mad when I tell neighbors who ask to use anything that if they are willing to work their way thru college, work hard for 24 years in the Navy, retire and start a second career, save money and not spend beyond their means, they could either afford to hire the work out or buy the item they want to borrow...
BTW- their are some good folks out their, I have a new neighbor who asked what my thoughts are on getting yard drainage around his new to him home fixed, he has some really bad drainage problems that is allowing water into his basement, I showed him my drain arrangement around my house and figured that is what he needed. Next day, he is out digging around his house with a shovel and pick, I go over and ask to help him and he politely said no, he would get it done and did not want to burden anybody else, I told him no burden on me, so we dig hard for about 8 hours that day, he never complained once. We might have got 15' about 6' down dug in some really hard clay. The next day, I bring my shovel and pick over, the backhoe, he was concerned that he could not afford to pay me, I told him no money, just be a good neighbor. I finished the dig out that day, he seemed overwhelmed that someone would do that. His wife baked me some bread and painted a watercolor of me on my backhoe, hmm, better than money to me, good neighbors that do not believe you own them something...
