Kinda depends. And depends upon how new it is and if you are worried about how it looks when you park next to the other tractors at the country club parking lot. If you broke it yourself, would you spend your money to fix it? Or to put it another way, if the guy didn't have a dime to his name and no insurance to collect, would you still spend your own money to fix it?
Kinda like a minor parking lot ding on an old car. At some point you are going to say that car isn't worth putting the money into it. Same for collecting a big chunk for hail damage on an old car. Sometimes better to take the cash and run.
If you answer no to the above and he is a friend then maybe tell him you need $50 to $100 bucks for the aggravation. Unless this is a show tractor or something. If it is just sitting out at the farm and will be for the next 20 years chances are you might break yourself at some point anyway. I've fixed many bumpers, windshields, door dings, etc. only to have something new happen a few months later.
I have borrowed trailers and loan out mine. I wouldn't loan it out if I was worried about some getting any dings in it. If it rolled in a ditch, hopefully he would have insurance. If it cut down a tire, I'd probably pro rate it unless I give it to him on baldies, then I wouldn't worry about it.
Only bad thing about a body shop is they want a fortune to fix and paint something anymore. I'd think about getting a plastic/fiberglass repair kit at wally world or autozone and a can of spray paint and fix it myself. He can pay for the materials. Put some reinforcing plastic behind it and use a mini torch to melt the plastic into place. Daughter let her boyfriend drive her car and he hit the curb and put a big tear in the bumper cover to where it was almost hanging on the ground. I drilled some holes, put in some pan head screws with brackets behind to pull the bumper cover in place and it does just fine. The crack pulled together and you wouldn't know it except for the screw heads. It's not like she is going to trade it any time soon anyway. Besides I already pocketed 2 grand from hail damage that you can only see when the sun is bright. Sometime I'm going to get some dry ice and try to remove the few dings that can be seen.
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Today's Featured Article - A Cautionary Tale - by Ian Minshull. In the early 1950s my father bought an Allis Chalmers B and I used it for all the row crop work with the mangolds and potatoes, rolling and the haymaking on our farm. The farm and the Allis were sold and I have spent a lifetime working on farms throughout the country. I promised myself that one day I would own an Allis. That time event
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